ABSTRACT
In the title compound, C21H19NO2S2, the seven-membered thia-zepine ring adopts a slightly distorted twist boat conformation. The dihedral angle between the benzene rings is 67.4â (2)°. The mean plane of the thio-phene ring is twisted by 59.3â (2) and 87.7â (2)° from the mean planes of the benezene rings. In the crystal, inversion dimers linked by pairs of C-Hâ¯O hydrogen bonds generate R 2 (2)(20) loops.
ABSTRACT
In the title compound, C21H23NO6S, the dihedral angle between the thio-pene and benzene rings is 88.66â (6)°. In the crystal, mol-ecules are connected by C-Hâ¯N and C-Hâ¯O hydrogen bonds, forming a tape along [10-1]. In addition, C-Hâ¯π and π-π stacking [centroid-centroid distance = 3.879â (2)â Å between the thio-phene rings] inter-actions are observed.
ABSTRACT
In the title compound, C13H7Cl3O2, the dihedral angle between the benzene rings is 82.1â (2)°. The dihedral angle between the CO2 group and its carbon-bonded ring is 14.50â (19)° In the crystal, aromatic π-π stacking inter-actions [minimum ring centroid separation = 3.604â (2)â Å] occur.
ABSTRACT
Fries rearrangement of substituted phenyl benzoates 1a-j to substituted hydroxy benzophenones 2a-j was achieved in excellent yield. Further benzoylation of 2a-j to benzoyloxy benzophenones 4a-n, a benzophenone analogue was achieved in good yield. All the newly synthesized compounds were evaluated for their anti-inflammatory activity and were compared with standard drugs. Out of the compounds studied, the compounds 4c, 4e, 4g, 4h and 4k with chloro and methyl substituents at para position showed more potent activity than the standard drugs at all doses tested.
Subject(s)
Anti-Inflammatory Agents, Non-Steroidal/chemical synthesis , Anti-Inflammatory Agents, Non-Steroidal/pharmacology , Benzophenones/chemical synthesis , Benzophenones/pharmacology , Animals , Anti-Inflammatory Agents, Non-Steroidal/toxicity , Benzophenones/toxicity , Carrageenan , Crystallography, X-Ray , Cyclooxygenase Inhibitors/chemical synthesis , Cyclooxygenase Inhibitors/pharmacology , Dose-Response Relationship, Drug , Edema/chemically induced , Edema/prevention & control , Lethal Dose 50 , Rabbits , Rats , Stomach Ulcer/chemically induced , Stomach Ulcer/pathologyABSTRACT
Precursors of podophyllotoxin were synthesized and screened for their antibacterial activity. The results proved that ethyl-2-(3'-methyl-4'-methoxybenzoyl)-3-(4â³ methoxyphenol)-cyclopropane-1-carboxylic acid and Ethyl-2-(3'-methyl-4'-methoxybenzyol-3-1 3â³, 4â³-dimethoxyphenyl)-cyclopropane-carboxylic acid have significant antibacterial activity against Citrobacter sp., Escherchia coli, Klebsiella pneumoniae, Pseudomonas aeruginosa, Salmonella typhi, Shigella sonnei and Streptococcus faecalis. The activity is lower than Ciprofloxacin and equal to Gentamicin and more than Penicillin and Streptomycin.
ABSTRACT
Benzophenones and its analogues are known for wide range of biological properties. Synthetic benzophenone analogue 2-benzoyl -phenoxy acetamide (BP-1) is proven to be potent antitumor and proapoptotic activity against EAT cells in-vivo. In the present report, we studied the antiangiogenic effect of BP-1 in EAT cells induced angiogenesis. Treatment with BP-1 in-vivo was demonstrated by the down regulation of the secretion of VEGF from EAT cells and inhibition of blood vessels formation indicating the potential angioinhibitory effect of BP-1 in EAT cells. HIF-1alpha protein, a transcription factor known to be key a regulator in hypoxia-induced angiogenesis was also down regulated by BP-1. Our findings indicated that, HIF-1alpha nuclear sequestration is repressed by BP-1 through inhibition of nuclear translocation. We postulate that diminished HIF-1alpha nuclear presence and activity in BP-1 treated EAT cells could be responsible for decreased VEGF expression and antiangiogenic effects.
Subject(s)
Acetamides/pharmacology , Angiogenesis Inhibitors/pharmacology , Antineoplastic Agents/pharmacology , Carcinoma, Ehrlich Tumor/metabolism , Chorioallantoic Membrane/drug effects , Hypoxia-Inducible Factor 1, alpha Subunit/drug effects , Neovascularization, Pathologic/prevention & control , Neovascularization, Physiologic/drug effects , Peritoneum/drug effects , Vascular Endothelial Growth Factor A/metabolism , Animals , Ascitic Fluid/chemistry , Cell Line, Tumor , Chick Embryo , Chorioallantoic Membrane/blood supply , Down-Regulation , Hypoxia-Inducible Factor 1, alpha Subunit/metabolism , Mice , Peritoneum/blood supply , Peritoneum/pathology , Protein Transport/drug effectsABSTRACT
A series of substituted benzophenone analogues, (2-aroyl-4-methylphenoxy)acetamides 4a-e, have been synthesized via three-step synthesis sequence beginning with the 2-hydroxybenzophenones 1a-e in excellent yield. 1a-e on reaction with ethyl chloroacetate afford ethyl (2-aroyl-4-methylphenoxy)acetates 2a-e which on alkaline hydrolysis afforded (2-aroyl-4-methylphenoxy)ethanoic acid 3a-e. Compounds 3a-e on condensation with p-chloroaniline furnished benzophenone analogues 4a-e. In the present report, we investigated the anti-tumor and proapoptotic effect of benzophenones in Ehrlich ascites tumor (EAT) cells. Treatment of benzophenones in vivo resulted in inhibition of proliferation of EAT cells and ascites formation. Further, we demonstrate that the induction of apoptosis in EAT cells is mediated through activation of caspase-3. These results suggest a further possible clinical application of these synthetic compounds as potent anti-tumor and proapoptotic compounds.
