- Base-Catalyzed Transesterification of Thionoesters
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Here we report a convenient synthesis of thionoesters by base-catalyzed transesterification. Benzyl and alkyl thionobenzoates and thionoheterobenzoates were efficiently prepared using various alcohols catalyzed by the corresponding sodium alkoxide. This methodology features a broad substrate scope, good to excellent yields, short reaction times, while simultaneously driving the reaction toward completion through the removal of the methanol byproduct. We also report the conversion of a small collection of thionobenzoates into the corresponding α,α-difluorobenzyl ethers to demonstrate the conversion of alcohols into difluorobenzyl or difluoroheterobenzyl ethers, a process that could prove useful for lead optimization in medicinal chemistry.
- Newton, Josiah J.,Britton, Robert,Friesen, Chadron M.
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p. 12784 - 12792
(2018/10/20)
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- Sulfocoumarin-, Coumarin-, 4-Sulfamoylphenyl-Bearing Indazole-3-carboxamide Hybrids: Synthesis and Selective Inhibition of Tumor-Associated Carbonic Anhydrase Isozymes IX and XII
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A series of sulfocoumarin-, coumarin-, and 4-sulfamoylphenyl-bearing indazole-3-carboxamide hybrids were synthesized and investigated as inhibitors of the human carbonic anhydrase (hCA, EC 4.2.1.1) isoforms I and II (cytosolic isozymes), as well as hCA IX and XII (transmembrane, tumor-associated enzymes). Compounds 6 a–g (amide derivatives) and 7 a–h (triazoles) act as “prodrugs”, and their hydrolysis products are the de facto CA inhibitors. These compounds displayed sub-micromolar to high-nanomolar inhibitory activity against hCA isoforms IX and XII, which were recently validated as antitumor drug targets. Moreover, no inhibition of the off-target hCA I and II isoforms was observed. Compounds 8 a–f (another set of triazoles) exhibited nanomolar inhibition against hCA isoforms I, II, IX and XII, among which compounds 8 c, 8 d, and 8 f were found to inhibit the tumor-associated hypoxia-induced hCA isoform IX with Ki values of 1.8, 2.3, and 2.0 nm respectively. Further exploration of these compounds could be useful for the development of novel antitumor agents with selective mechanisms of CA inhibitory action.
- Angapelly, Srinivas,Sri Ramya,Angeli, Andrea,Supuran, Claudiu T.,Arifuddin, Mohammed
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p. 1578 - 1584
(2017/10/16)
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- Synthesis of new α aminophosphonate system bearing Indazole moiety and their biological activity
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We are reporting herein for the first time the synthesis of α-aminophosphonates containing Indazole moiety in two steps. In the first step, imines of substituted N-benzylidene-1-methyl-1H-indazole-3-carbohydrazide are synthesized and in the next step it h
- Ali, Nasir Ali Shafakat,Zakir, Shaikh,Patel, Muqtadir,Farooqui, Mazahar
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experimental part
p. 39 - 43
(2012/07/02)
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- Efficient syntheses of exo-granisetron hydrochloride and other potential impurities present in granisetron hydrochloride, an anti-emetic drug
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European Pharmacopeia mentions about nine potential impurities in Granisetron hydrochloride. These impurities need to be controlled in the API as described in the Pharmacopeia. Elegant syntheses of four potential impurities in Granisetron hydrochloride are disclosed.
- Vishnu, Eda V.R.,Joseph, Suju,Srinivasana, Abayee K.,Gania, Ramesh S.,Reddy, Govindabur R.,Rao, Patakokila V.,Dahanukara, Vilas H.,Ramanatham, Josyula,Devanna, Nayakanti
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experimental part
p. 722 - 727
(2012/05/04)
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- Fab I inhibitors
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Compounds of formula (I) and (II) are disclosed wherein, R1, R2, R3, R4, X, A, B, D and Q are as disclosed in the specification, and the compounds are FabI inhibitors useful in the treatment of bacterial infecti
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Page column 18
(2010/02/06)
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- DERIVATIVES OF AMIDE ANALOGS OF CERTAIN METHANO BRIDGED QUINOLIZINES
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This invention relates to novel amide derivatives of certain 2, 6-methano-2H-quinolizine-type compounds, to the intermediates and processes for their preparation, to their ability to antagonize the effects of serotonin at the 5HT 3 receptors, and to their end-use application in the treatment of chemotherapeutically-induced nausea and vomiting, as anti-anxiety agents, in the symptomatic treatment of pain associated with migraine, as anti-arrhythmic agents, in the treatment of cognitive disorders, in treating hallucinatory endogenous psychoses of the type manifested in patients suffering from schizophrenia, and mania, in the treatment of glaucoma, for stimulating gastric motility, to combat drug abuse, to treat sleep apnea and to treat irritable bowel syndrome.
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