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1.
J Org Chem ; 81(13): 5354-61, 2016 07 01.
Article in English | MEDLINE | ID: mdl-27183100

ABSTRACT

1,3,5-Trioxane-2,4,6-trione (cyclic trimer of CO2) is the product of a four-step synthesis: chlorination of isobutyraldehyde; cyclotrimerization of 2-chloro-2-methylpropanal; dehydochlorination of 2,4,6-tris(2-chloropropan)-2-yl-1,3,5-trioxane; ozonolysis at -80 °C of 2,4,6-tri(propan-2-ylidene)-1,3,5-trioxane. This trioxane-trione is detected in solution at temperatures between -80 to -40 °C, and its conversion to CO2 is monitored by (13)C NMR and FTIR. The CO2 trimer has a half-life of approximately 40 min at -40 °C.

2.
Bioorg Med Chem Lett ; 17(5): 1346-8, 2007 Mar 01.
Article in English | MEDLINE | ID: mdl-17188865

ABSTRACT

Quaternized chlorpromazine, triflupromazine, and promethazine derivatives were synthesized and examined as antitubercular agents against both actively growing and non-replicating Mycobacterium tuberculosis H37Rv. Impressively, several compounds inhibited non-replicating M. tuberculosis at concentrations equal to or double their MICs against the actively growing strain. All active compounds were non-toxic toward Vero cells (IC50 > 128 microM). N-Allylchlorpromazinium bromide was only weakly antitubercular, but replacing allyl with benzyl or substituted benzyl improved potency. An electron-withdrawing substituent on the phenothiazine ring was also essential. Branching at the carbon chain decreased antitubercular activity. The optimum antitubercular structures possessed N-(4- or 3-chlorobenzyl) substitution on triflupromazine.


Subject(s)
Antitubercular Agents/chemical synthesis , Antitubercular Agents/pharmacology , Chlorpromazine/chemical synthesis , Chlorpromazine/pharmacology , Mycobacterium tuberculosis/drug effects , Promazine/chemical synthesis , Promazine/pharmacology , Promethazine/chemical synthesis , Promethazine/pharmacology , Quaternary Ammonium Compounds/chemical synthesis , Quaternary Ammonium Compounds/pharmacology , Structure-Activity Relationship , Triflupromazine/chemical synthesis , Triflupromazine/pharmacology
3.
Inorg Chem ; 45(5): 2242-50, 2006 Mar 06.
Article in English | MEDLINE | ID: mdl-16499390

ABSTRACT

Ligands of intermediate steric bulk were designed to mimic metalloenzymes with histidine and carboxlyate binding sites. The reaction between tris(3-isopropylpyrazolyl)methane and butyllithium followed by SO3NMe3 in THF yielded the new ligand lithium tris(3-isopropylpyrazolyl)methane sulfonate (LiTpmsiPr). Various metal salts reacted with LiTpmsiPr to give the octahedral complexes M(TpmsiPr)2 (M = Zn, Cu, Ni, Co, Fe) in which each ligand has N,N,O binding to the metal. In the reaction between LiTpmsiPr and ZnCl2, in addition to the major product Zn(TpmsiPr)2, [LiTpmsiPrZnCl2].2THF was also formed as a minor product with a tetrahedral zinc atom coordinated to either N,N,Cl,Cl in the solid phase or N,N,N,Cl in acetonitrile solution. Although TpmsiPr is coordinatively flexible and can act as a bipodal or tripodal ligand, it appears to favor the formation of octahedral L2M complexes.


Subject(s)
Chemistry, Inorganic/methods , Enzymes/chemistry , Enzymes/metabolism , Metals/metabolism , Models, Chemical , Binding Sites , Cobalt , Copper , Iron , Ligands , Magnetic Resonance Spectroscopy , Metals/chemistry , Molecular Structure , Nickel , Nitrogen/chemistry , Nitrogen/metabolism , Oxygen/chemistry , Oxygen/metabolism , Pyrazoles/chemistry , Solubility , Spectrophotometry, Ultraviolet , Sulfonic Acids/chemistry , Zinc
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