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1.
Adv Exp Med Biol ; 1232: 85-90, 2020.
Article in English | MEDLINE | ID: mdl-31893398

ABSTRACT

Delayed orthostatic hypotension (OH) is a minor subset of orthostatic dysregulation (OD). Cerebral blood oxygenation in juvenile patients with delayed OH has not been studied. We investigated the bilateral changes in cerebral oxygenation in the prefrontal cortex during an active standing test in 23 juvenile patients with delayed OH using near-infrared spectroscopy (NIRS). We measured the oxy-Hb, deoxy-Hb, and total-Hb during the active standing test. Four observations were made during the test: t1 in a resting supine position, t2 when maintaining blood pressure, and the remaining two (t3, t4) during hypotension. The concentration of oxy-Hb significantly decreased prior to satisfying the diagnostic criteria of delayed OH after standing and did not change thereafter. The concentration of deoxy-Hb increased gradually during the measurement periods. In addition, total-Hb increased from t2 to t3. There was no significant difference in the change in each Hb parameter between the left and right cerebral hemispheres. Our results indicate that NIRS parameters are more sensitive than blood pressure for the interpretation of cerebral autoregulation in juvenile patients with delayed OH.


Subject(s)
Cardiovascular System , Cerebrovascular Circulation , Hypotension, Orthostatic , Oxygen , Standing Position , Adolescent , Blood Pressure , Cerebrovascular Circulation/physiology , Humans , Hypotension, Orthostatic/blood , Hypotension, Orthostatic/diagnosis , Oxygen/blood , Spectroscopy, Near-Infrared
2.
Orthod Craniofac Res ; 20(4): 209-215, 2017 Nov.
Article in English | MEDLINE | ID: mdl-28921849

ABSTRACT

OBJECTIVES: To investigate the effects of pre-surgical nasoalveolar moulding (PNAM) on the maxillary arch and nasal form in patients with unilateral cleft lip and palate (UCLP). SETTING AND SAMPLE POPULATION: This is a retrospective case series study. The subjects were infants with complete UCLP who were treated with PNAM (n = 18) at Kagoshima University Medical and Dental Hospital (Japan) between 2006 and 2013. MATERIAL AND METHODS: Maxillary dental casts and facial photographs were taken at the time of the first visit and immediately prior to lip surgery to evaluate the maxillary arch and nasal form changes. The dental casts were scanned with a laser scanner, and changes in the 3-Dimensional coordinates of anatomical landmarks and alveolar cleft width were analysed. Moreover, we investigated the correlation between the changes in the maxillary alveolar arch and nasal form. RESULTS: Regarding the maxillary alveolar arch form, the anterior points of the major segment had moved significantly to the cleft side just prior to the time of lip repair, and the alveolar cleft width was significantly decreased. For nasal form, the inclination and displacement of the columella were significantly improved. The improvement of columella inclination was moderately correlated with the posterior movement of the anterior points of the major segment. CONCLUSIONS: These findings indicate that PNAM for infants with UCLP enhanced symmetry in the maxillary alveolar arch and nasolabial form. In addition, the posterior movement of the anterior points of the maxillary alveolar arch was correlated with the improvement of columella deformation.


Subject(s)
Alveolar Process , Cleft Lip/surgery , Cleft Palate/surgery , Dental Arch , Nasal Septum , Preoperative Care/methods , Female , Humans , Infant , Male , Retrospective Studies
4.
Colorectal Dis ; 18(8): 795-802, 2016 Aug.
Article in English | MEDLINE | ID: mdl-26784017

ABSTRACT

AIM: Sessile serrated adenomas/polyps (SSA/Ps) have been proposed as precursors of colorectal cancer. The aims of this investigation were to compare the endoscopic findings of SSA/Ps with those of other serrated lesions and to compare the histological findings of SSA/Ps with those of conventional adenomas. METHOD: We retrospectively reviewed colonoscopy records at our institution from 1984 to 2013 and identified cases of endoscopically or surgically resected conventional adenomas and serrated lesions, including SSA/Ps, hyperplastic polyps (HPs) and traditional serrated adenomas (TSAs). The colonoscopic findings of SSA/Ps were compared with those of the other two serrated lesions and histological findings were compared among all groups of lesions. RESULTS: There were 79 HPs in 68 patients, 77 SSA/Ps in 63 patients, 167 TSAs in 145 patients and 6324 conventional adenomas in 4129 patients. The inverted type and flat-elevated type were more frequent among SSA/Ps than among the other two types of serrated lesions. Magnifying colonoscopy revealed that a round and open pit pattern, expanded crypt openings and varicose microvascular vessels were more frequently observed among SSA/Ps than among the other types. The incidence of high-grade dysplasia or carcinoma among SSA/Ps (13.0%) was significantly higher than that among HPs (0%, P < 0.001) and equivalent to that among conventional adenomas (12.3%). CONCLUSION: SSA/Ps have colonoscopic features distinct from those of HPs and TSAs. The malignant potential of SSA/Ps seems to be equal to that of conventional adenomas.


Subject(s)
Adenocarcinoma/pathology , Adenoma/pathology , Colonic Polyps/pathology , Colonoscopy , Colorectal Neoplasms/pathology , Microvessels/pathology , Adenocarcinoma/blood supply , Adenocarcinoma/complications , Adenoma/blood supply , Adenoma/complications , Aged , Colon/pathology , Colorectal Neoplasms/blood supply , Colorectal Neoplasms/complications , Female , Humans , Hyperplasia , Male , Middle Aged , Retrospective Studies
6.
Lupus ; 22(10): 1056-9, 2013 Sep.
Article in English | MEDLINE | ID: mdl-23861027

ABSTRACT

This case report describes a Japanese girl with systemic lupus erythematosus who had recurrent fevers and erythema nodosum. She was later found to carry the complex allele E148Q/R202Q/P369S/R408Q of MEFV, the gene responsible for familial Mediterranean fever.


Subject(s)
Familial Mediterranean Fever/complications , Lupus Erythematosus, Systemic/complications , C-Reactive Protein/analysis , Child , Cytoskeletal Proteins/genetics , Familial Mediterranean Fever/genetics , Female , Humans , Lupus Erythematosus, Systemic/genetics , Pyrin
8.
Neuroscience ; 194: 160-9, 2011 Oct 27.
Article in English | MEDLINE | ID: mdl-21871540

ABSTRACT

BACKGROUND: Spasticity and rigidity are serious complications associated with spinal traumatic or ischemic injury. Clinical studies show that tizanidine (Tiz) is an effective antispasticity agent; however, the mechanism of this effect is still not clear. Tiz binds not only to α2-adrenoreceptors (AR) but also to imidazoline (I) receptors. Both receptor systems (AR+I) are present in the spinal cord interneurons and α-motoneurons. The aim of the present study was to evaluate the therapeutic potency of systematically or spinally (intrathecally [IT]) delivered Tiz on stretch reflex activity (SRA) in animals with ischemic spasticity, and to delineate supraspinal or spinal sites of Tiz action. EXPERIMENTAL PROCEDURES: Animals were exposed to 10 min of spinal ischemia to induce an increase in SRA. Increase in SRA was identified by simultaneous increase in recorded electromyography (EMG) activity and ankle resistance measured during computer-controlled ankle dorsiflexion (40°/3 s) in fully awake animals. Animals with increased SRA were divided into several experimental subgroups and treated as follows: (i) Tiz administered systemically at the dose of 1 mg kg(-1), or IT at 10 µg or 50 µg delivered as a single dose; (ii) treatment with systemic Tiz was followed by the systemic injection of vehicle, or by nonselective AR antagonist without affinity for I receptors; yohimbine (Yoh), α2A AR antagonist; BRL44408 (BRL), α2B AR antagonist; ARC239 (ARC), nonselective AR and I(1) receptor antagonist; efaroxan (Efa), or nonselective AR and I(2) receptor antagonist; idazoxan (Ida); (iii) treatment with IT Tiz was followed by the IT injection of selective α2A AR antagonist; atipamezole (Ati). In a separate group of spastic animals the effect of systemic Tiz treatment (1 mg/kg) or isoflurane anesthesia on H-reflex activity was also studied. RESULTS: Systemic and/or IT treatment with Tiz significantly suppressed SRA. This Tiz-mediated anti-SRA effect was reversed by BRL (5 mg kg(-1)), Efa (1 mg kg(-1)), and Ida (1 mg kg(-1)). No reversal was seen after Yoh (3 mg kg(-1)) or ARC (5 mg kg(-1)) treatment. Anti-SRA induced by IT Tiz (50 µg) was reversed by IT injection of Ati (50 µg). Significant suppression of H-reflex was measured after systemic Tiz treatment (1 mg/kg) or isoflurane (2%) anesthesia, respectively. Immunofluorescence staining of spinal cord sections taken from animals with spasticity showed upregulation of α2A receptor in activated astrocytes. CONCLUSIONS: These data suggest that α2A AR and I receptors, but not α2B AR, primarily mediate the Tiz-induced antispasticity effect. This effect involves spinal and potentially supraspinal sites and likely targets α2A receptor present on spinal neurons, primary afferents, and activated astrocytes. Further studies using highly selective antagonists are needed to elucidate the involvement of specific subtypes of the AR and I receptors in the antispasticity effect seen after Tiz treatment.


Subject(s)
Clonidine/analogs & derivatives , Paraplegia/drug therapy , Paraplegia/physiopathology , Reflex, Stretch/drug effects , Spinal Cord Ischemia/physiopathology , Animals , Chronic Disease , Clonidine/pharmacology , Disease Models, Animal , Male , Muscle Relaxants, Central/pharmacology , Neural Inhibition/drug effects , Neural Inhibition/physiology , Paraplegia/etiology , Rats , Rats, Sprague-Dawley , Reflex, Stretch/physiology , Spinal Cord Ischemia/complications
9.
Kyobu Geka ; 64(5): 359-63, 2011 May.
Article in Japanese | MEDLINE | ID: mdl-21591434

ABSTRACT

We present a case of a 14-year-old male with incessant idiopathic ventricular tachycardia for which both pharmacological and catheter ablation treatments failed. Curative surgery was performed on this patient. By intraoperative epicardial isochronous mapping, arrhythmogenic focus was identified in the right ventricular infundibulum between the large conus branch and the proximal right ventricular coronary branch. After cryoablation both from the epi- and endo-cardial sides failed to terminate the arrhythmia, subsequent full-thickness resection of the identified focus was performed. There was no postoperative recurrence of tachyarrhythmia In idiopathic ventricular tachycardia, arrhythmogenic focus is not always situated on the endo- or epicardial side. Full-thickness resection of the focus site might be necessary in such patients as we experienced this time.


Subject(s)
Heart Ventricles/surgery , Tachycardia, Ventricular/surgery , Adolescent , Cardiac Surgical Procedures/methods , Catheter Ablation , Humans , Male
10.
Kyobu Geka ; 64(5): 410-3, 2011 May.
Article in Japanese | MEDLINE | ID: mdl-21591445

ABSTRACT

A 64-year-old male with giant left atrium and giant coronary sinus, who had aortic valve regurgitation, prosthesis valve paravalvular leakage in mitral position and prosthesis valve malfunction in tricuspid valve position, was successfully treated with double valve replacement, paravalvular leakage repair and volume reduction of left atrium and coronary sinus. Giant coronary sinus was about 70 mm in diameter and was thought to be induced by persistent left superior vena cava, high right atrium pressure and prosthesis valve malfunction in tricuspid valve position. Lung volume was so much increased by volume reduction of left atrium and coronary sinus and patient's symptoms were much improved.


Subject(s)
Coronary Sinus/abnormalities , Coronary Sinus/surgery , Heart Valve Diseases/surgery , Heart Atria/abnormalities , Heart Valve Diseases/complications , Humans , Male , Middle Aged
11.
Kyobu Geka ; 62(12): 1056-60, 2009 Nov.
Article in Japanese | MEDLINE | ID: mdl-19894570

ABSTRACT

We report a very high risk case of reoperation for pseudoaneurysm after ascending aortic replacement for acute aortic dissection in a 78-year-old man with chronic renal failure and disseminated intravascular coagulation (DIC). Computed tomography 5 years after the 1st operation showed huge pseudoaneurysm originated from the distal anastomosis and the angiogram showed moderate aortic regurgitation. Hemodialysis and congestive heart failure associated with DIC complicated his general condition. Preoperative DIC score was 7 with D-dimer of 39.8 microg/ml. The patient underwent reoperation through night anterior thoracotomy. At 20 degrees C of urinary bladder temperature, we started re-median sternotomy and ablated the adhesion. When the pseudoaneurysm ruptured, we started hypothermic circulatory arrest with selective cerebral perfusion immediately. And Bentall operation and hemi-arch replacement were performed. Postoperative recovery required long period and he was transferred to another hospital at 3 months after the surgery. Postoperative data showed reduction of DIC score to 3.


Subject(s)
Aneurysm, False/etiology , Aneurysm, False/surgery , Aortic Aneurysm/surgery , Aortic Dissection/surgery , Disseminated Intravascular Coagulation/etiology , Kidney Failure, Chronic/complications , Aged , Humans , Male , Postoperative Complications , Reoperation
12.
Br J Anaesth ; 96(1): 88-94, 2006 Jan.
Article in English | MEDLINE | ID: mdl-16317029

ABSTRACT

BACKGROUND: Intrathecal (IT) morphine given after a short interval of aortic occlusion in a rodent model induced transient spastic paraparesis via opioid receptor-predicted actions in spinal cord. To determine the role(s) of spinal opioid receptor subtypes we investigated whether IT administration of various selective opioid receptor agonists can induce paraparesis following a short period of spinal cord ischaemia in rats. METHODS: In Sprague-Dawley rats implanted with an IT catheter, spinal cord ischaemia was induced for 6 min using an intraaortic balloon. Mu ([D-Ala2, N-Me Phe4, Gly-ol5] enkephalin), kappa (U50488H) or delta ([D-Pen(2,5)] enkephalin) selective agonists were injected intrathecally 30 min after reperfusion. A separate group of animals was used to investigate the dose-response effect on this motor dysfunction. For this purpose, three doses of mu, kappa, or delta agonists were injected intrathecally after ischaemia. After IT injection, recovery of motor function was assessed periodically using the motor deficit index (0=complete recovery; 6=complete paraplegia). RESULTS: IT administration of mu and delta but not kappa agonists produced dose-dependent effects in the induction of spastic paraparesis. In addition, this spasticity induced by IT mu and delta agonists was reversed completely by IT naloxone and naltrindole, respectively. CONCLUSION: These results suggest that the effect of various opioids on motor function after a short period of spinal cord ischaemia depends upon individual opioid receptor subtypes.


Subject(s)
Analgesics, Opioid/toxicity , Paraparesis, Spastic/chemically induced , Receptors, Opioid, delta/agonists , Receptors, Opioid, mu/agonists , Spinal Cord Ischemia/complications , 3,4-Dichloro-N-methyl-N-(2-(1-pyrrolidinyl)-cyclohexyl)-benzeneacetamide, (trans)-Isomer/pharmacology , Analgesics, Non-Narcotic/toxicity , Animals , Dose-Response Relationship, Drug , Enkephalin, Ala(2)-MePhe(4)-Gly(5)-/pharmacology , Enkephalin, D-Penicillamine (2,5)-/pharmacology , Injections, Spinal , Male , Movement/drug effects , Paraparesis, Spastic/etiology , Rats , Rats, Sprague-Dawley , Receptors, Opioid, delta/physiology , Receptors, Opioid, kappa/agonists , Receptors, Opioid, kappa/physiology , Receptors, Opioid, mu/physiology , Spinal Cord Ischemia/pathology
13.
Scand J Gastroenterol ; 39(2): 111-8, 2004 Feb.
Article in English | MEDLINE | ID: mdl-15000271

ABSTRACT

BACKGROUND: The role of Helicobacter pylori infection in rheumatoid arthritis (RA) patients during treatment with non-steroidal anti-inflammatory drugs (NSAID) is still unclear. METHODS: By means of endoscopy and biopsy, gastroduodenal lesions and H. pylori status were repeatedly examined in 88 RA patients at intervals ranging from 26 to 49 months. Histology and culture were applied to determine H. pylori status. Serial changes in gastroduodenal lesions and histologic score for mucosal atrophy were compared among groups classified by initial and second H. pylori status. RESULTS: There were 28 patients with continuously positive H. pylori infection (CP group), 33 patients with continuously negative H. pylori infection (CN group), 7 patients in whom H. pylori status became negative (PN group), and 20 patients in whom H. pylori status could not be determined (UD group). Age, duration and species of NSAID, disease activity of RA, gastroprotective drugs applied and the prevalence of gastroduodenal mucosal lesions were not different among the groups at either the initial or the second examination. In the PN group, the score for mucosal atrophy at the second examination was significantly lower than at the initial examination, whereas no difference was found for the CP, CN and UD groups. Overall, histologic score for mucosal atrophy was higher in H. pylori-positive patients than in H. pylori-negative patients at both initial and second examination. CONCLUSIONS: In RA patients using NSAIDs, H. pylori infection may not affect the course of gastroduodenal lesions and activity of RA, but the infection contributes to mucosal atrophy.


Subject(s)
Anti-Inflammatory Agents, Non-Steroidal/adverse effects , Arthritis, Rheumatoid/drug therapy , Gastric Mucosa/pathology , Helicobacter Infections/complications , Helicobacter pylori , Peptic Ulcer/etiology , Adult , Aged , Anti-Inflammatory Agents, Non-Steroidal/therapeutic use , Arthritis, Rheumatoid/complications , Atrophy/etiology , Endoscopy, Digestive System , Female , Helicobacter Infections/diagnosis , Helicobacter pylori/isolation & purification , Humans , Male , Middle Aged , Peptic Ulcer/microbiology , Peptic Ulcer/pathology
14.
Endoscopy ; 35(4): 363-5, 2003 Apr.
Article in English | MEDLINE | ID: mdl-12664397

ABSTRACT

Inflammatory myoglandular polyp is an uncommon benign colorectal polyp. We treated nine cases of histologically verified inflammatory myoglandular polyp. The polyps were identified as a pedunculated protrusion located in the distal part of the large intestine. On colonoscopy, eight polyps had a smooth, spherical, and hyperemic surface, accompanied by a patchy mucous exudate. Magnification endoscopy revealed a rugged surface composed of smooth nodules. These colonoscopic findings corresponded to hyperplastic glands with occasional cystic dilation and inflamed stroma with proliferation of smooth-muscle fibers. Inflammatory myoglandular polyp appears to be a distinctive clinical entity, with a unique appearance on colonoscopy.


Subject(s)
Colonic Polyps/surgery , Adult , Aged , Colonic Polyps/diagnosis , Colonic Polyps/pathology , Female , Humans , Male , Middle Aged , Rectal Diseases/diagnosis , Rectal Diseases/pathology , Rectal Diseases/surgery
15.
Rheumatology (Oxford) ; 41(1): 72-7, 2002 Jan.
Article in English | MEDLINE | ID: mdl-11792883

ABSTRACT

OBJECTIVE: The aim of this study was to investigate the impact of Helicobacter pylori infection on clinical features in patients with rheumatoid arthritis (RA) under medication with non-steroidal anti-inflammatory drugs. METHODS: One hundred and eighty-four patients with RA were tested for the presence of H. pylori infection. Clinical features and gastroduodenal lesions were compared between H. pylori-positive and -negative patients. RESULTS: One hundred and thirteen patients were positive and 71 patients were negative for H. pylori. The age, severity of RA, prevalence of gastrointestinal symptoms and gastroduodenal lesions and the class of gastroprotective drugs were not different between the two groups. Reflux oesophagitis was less frequent and sulphasalazine was less frequently administered in the H. pylori-positive group. CONCLUSIONS: The severity of RA, prevalence of gastroduodenal lesions other than reflux oesophagitis and the application of gastroprotective drugs do not seem to depend upon H. pylori infection in RA patients. Sulphasalazine may be protective against H. pylori infection.


Subject(s)
Anti-Inflammatory Agents, Non-Steroidal/adverse effects , Arthritis, Rheumatoid/drug therapy , Arthritis, Rheumatoid/epidemiology , Gastroenteritis/chemically induced , Helicobacter Infections/epidemiology , Helicobacter pylori/isolation & purification , Adult , Aged , Aged, 80 and over , Anti-Inflammatory Agents, Non-Steroidal/administration & dosage , Arthritis, Rheumatoid/diagnosis , Cohort Studies , Comorbidity , Endoscopy, Gastrointestinal , Female , Gastric Mucosa/drug effects , Gastric Mucosa/pathology , Gastroenteritis/pathology , Helicobacter Infections/diagnosis , Helicobacter Infections/drug therapy , Humans , Intestinal Mucosa/drug effects , Intestinal Mucosa/pathology , Male , Middle Aged , Prevalence , Probability , Risk Factors , Statistics, Nonparametric
16.
Mod Rheumatol ; 12(1): 72-5, 2002 Mar.
Article in English | MEDLINE | ID: mdl-24383836

ABSTRACT

Abstract We report the youngest known girl with acute lupus hemophagocytic syndrome (ALHS) at the onset of her illness. We investigated the pathogenesis of ALHS by assessment of factors thought to influence the onset, such as cytokines, Th1/Th2 balance, immune complexes, and autoantibodies. A girl 8 years and 10 months old with systemic lupus erythematosus (SLE) had high fever, pancytopenia, and hemophagocytosis in the bone marrow. We diagnosed SLE complicated by ALHS. Treatment with predonisolone (2 mg/kg/day) was started, and her clinical features improved. Th2 dominance of the Th1/Th2 balance, hypocomplementemia, and high levels of anti-ds-DNA antibody, PAIgG, and immune complexes were seen, but no hypercytokinenemia, hyperferritinemia, or hypertriglyceridemia. ALHS at the onset of SLE, excluding that caused by infections, could be a form of reactive hemophagocytosis caused by excessive production of autoantibodies and immune complexes. High-dose steroid therapy is effective without need for immunosuppressive drugs. Our patient showed hypocomplementemia along with high levels of anti-dsDNA antibody, anticardiolipin antibody, platelet-associated IgG (PAIgG), and immune complexes. The autoimmune-associated hemophagocytic syndrome (AAHS) is thought to involve an autoantibody-mediated mechanism or an immune complex-mediated mechanism. On the basis of our data, ALHS could simultaneously involve both these mechanisms. We demonstrated that there was no hypercytokinemia and no hyperferritinemia in ALHS associated with Th2 dominance. Autoantibodies and immune complexes may cause histiocytic hemophagocytosis in ALHS. High-dose steroids and high-dose immunoglobulin are effective but immunosuppressive drugs are not needed.

17.
J Org Chem ; 66(23): 7691-5, 2001 Nov 16.
Article in English | MEDLINE | ID: mdl-11701022

ABSTRACT

Anodic monofluorination at the position alpha to the oxygen atom of the (E)-3-benzylidene-2,3-dihydrochroman-4-one derivatives was successfully carried out to provide the corresponding 2-fluorochromanones selectively. This is the first regioselective electrochemical fluorination of fused-type, oxygen-containing heterocyclic compounds. Anodic fluorination of a chromone derivative also gave a similar fluorinated chromanone stereoselectively.

18.
Scand J Gastroenterol ; 36(11): 1134-40, 2001 Nov.
Article in English | MEDLINE | ID: mdl-11686211

ABSTRACT

BACKGROUND: The significance of atrophy in the background mucosa and Helicobacter pylori infection in the morphogenesis of gastric epithelial tumors has not yet been investigated. METHODS: The degree of mucosal atrophy, as determined by a histological analysis and the serum pepsinogen (PG) levels, and H. pylori status were investigated in patients with elevated adenoma (EA group; n = 40), elevated early cancer of intestinal type (ECI group; n = 30), depressed early cancer of intestinal type (DCI group; n = 37) and depressed early cancer of diffuse type (DCD group; n = 33), and the findings were then compared to those in 91 controls. RESULTS: At all sites of the stomach, the histologic score of atrophy was higher in the EA group and in the ECI group than in the controls. In the DCI group, the histologic score of atrophy in the antrum was higher than in the controls, but no such difference in the score was found in the DCD group. The PG I/II ratios in the EA, ECI and DCI groups were significantly lower than in the controls, and the value was also different between the ECI and DCI groups. While H. pylori prevalence was higher in all groups than in the controls, a logistic regression analysis which included the grade of atrophy as a determinant revealed the infection to be an independent associated factor for the DCD group. CONCLUSIONS: The difference in the background mucosal atrophy seems to contribute to different macroscopic types in gastric epithelial tumors. This seems to be the case especially for cancer of intestinal type.


Subject(s)
Gastric Mucosa/pathology , Stomach Neoplasms/pathology , Adenoma/pathology , Aged , Atrophy , Female , Helicobacter Infections/pathology , Helicobacter pylori , Humans , Male , Middle Aged , Pepsinogen A/blood , Regression Analysis
19.
J Org Chem ; 66(21): 7020-4, 2001 Oct 19.
Article in English | MEDLINE | ID: mdl-11597223

ABSTRACT

Anodic fluorination of N-benzoyl, N-acethyl-, and N-formylthiazolidine derived from L-cysteine was carried out in dimethoxyethane (DME) and acetonitrile containing various supporting fluoride salts using an undivided cell. Highly regioselective fluorination proceeded to provide the corresponding 5-monofluorinated thiazolidine derivatives in good yields in DME, and the diastereoselectivitiy was moderate to high regardless of the supporting fluoride salts. The diastereoselectivitiy of the fluorination was greatly affected by the bulkyness of the subsitituent on the nitrogen atom, and N-benzoylthiazolidine gave much higher diastereoselectivity compared with N-formyl derivative. The fluorination of the thiazolidines was not achieved by commercially available fluorinating reagents such as N-fluoropyridinium salts.


Subject(s)
Fluorides/chemical synthesis , Thiazoles/chemical synthesis , Electrochemistry , Electrodes , Electrolysis
20.
J Org Chem ; 66(21): 7030-4, 2001 Oct 19.
Article in English | MEDLINE | ID: mdl-11597225

ABSTRACT

Anodic fluorination of (E)-3-benzylidene-2,3-dihydrothiochroman-4-one and 3-benzyl-1-thiochromone derivatives under a variety of electrolytic conditions was found to provide selectively or exclusively the same fluorinated products: (E)-3-benzylidene-2,3-dihydro-2-fluorothiochroman-4-ones. In addition, di- and trifluorinated derivatives were also obtained depending on the starting heterocycles and electrolytic conditions. The factors affecting the product selectivity were also examined.

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