27545-53-5

Upstream product

• 2227-79-4 benzenecarbothioamide 
• 624-49-7 dimethylfumarate 
• 73501-01-6 2,2-bis(trichloromethyl)-5-phenyl-1,3,4-oxathiazole 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 73501-00-5 5-phenyl-2-trichloromethyl-1,3,4-oxathiazole 
• 14730-25-7 3-phenyl-1,4,2-dithiazole-5-thione 
• 55-21-0 benzamide 
• 2168-78-7 methyl dithiobenzoate 
• 5852-49-3 5-phenyl-1,3,4-oxathiazol-2-one 
• 60027-35-2 4-phenyl-1,3,2-oxathiazolylium-5-olate 
• 14730-26-8 5-phenyl-1,3,4-dithiazol-2-one 
• 62157-38-4 S,S-diphenyl-N-thiobenzoyl-sulfimide 
• 56973-71-8 N-benzyl-imidosulfurous acid difluoride 
• 67048-45-7 3-phenyl-4,5-dihydro-isothiazole-4r,5t-dicarboxylic acid dimethyl ester 

Downstream Products

• 76240-12-5 methyl 5-<(NN'-diphenylamidino)carbamoyl>-3-phenylisothiazole-4-carboxylate 
• 92126-32-4 3-phenyl-4,5-bis(hydroxymethyl)isothiazole 
• 92126-33-5 3-phenyl-4,5-bis(hydroxymethyl)isothiazole bis(methylcarbamate) 
• 1172590-16-7 4,7-dihydroxy-3-phenyl-isothiazolo[4,5-c]pyridine-6-carboxylic acid methyl ester 
• 1172590-14-5 4,7-dihydroxy-3-phenyl-isothiazolo[5,4-c]pyridine-5-carboxylic acid methyl ester 
• 1172590-12-3 4,7-dihydroxy-3-phenyl-isothiazolo[4,5-c]pyridine-6-carboxylic acid butyl ester 
• 1172590-10-1 4,7-dihydroxy-3-phenyl-isothiazolo[5,4-c]pyridine-5-carboxylic acid butyl ester 
• 126244-34-6 3-phenyl-isothiazole-4,5-dicarboxylic acid 4-methyl ester 
• 1172590-07-6 3-phenyl-isothiazole-4,5-dicarboxylic acid 5-methyl ester 
• 1172590-08-7 N-(2-methoxy-2-oxoethyl)-4-carbamoyl-3-phenyl-isothiazole-5-carboxylic acid methyl ester 
• 1172590-09-8 N-(2-methoxy-2-oxoethyl)-5-carbamoyl-3-phenyl-isothiazole-4-carboxylic acid methyl ester 
• 27545-55-7 3-phenylisothiazole-4-carbonyl chloride 
• 18160-81-1 3-phenyl-isothiazole-4-carboxylic acid amide 
• 27545-54-6 3-phenyl-isothiazole-4,5-dicarboxylic acid 

Relevant academic research and scientific papers

Microwave-assisted generation and reactions of nitrile sulfides

An improved practical method is described for the generation of benzonitrile sulfide based on microwave-assisted decarboxylation of 5-phenyl-1,3,4-oxathiazol-2-one. Reaction times for the preparation of cycloadducts (e.g. isothiazoles and 1,2,4-thiadiazoles) derived from the nitrile sulphide are reduced from typically 15-30 h to approximately 15 min.

HISTONE DEACETYLASE INHIBITORS AND COMPOSITIONS AND METHODS OF USE THEREOF

Provided are certain histone deacetylase (HDAC) inhibitors of Formula I, or pharmaceutically acceptable salts thereof, compositions thereof, and methods of their use. The condition or disorder mediated by HDAC comprises a neurodegenerative pathology. Accordingly, also provided is a method of treating a neurodegenerative pathology mediated by HDAC in a subject in need of such a treatment, comprising administering to the subject a therapeutically effective amount of at least one compound, or pharmaceutically acceptable salt thereof, described herein.

Nitrile Sulfides Part 16.1,2Synthesis of 1,2-benzisothiazolesvia nitrile sulfide cycloaddition reactions

The cycloaddition reactions of nitrile sulfides have been used to prepare benzisothiazole quinones and 1,2-benzisothiazole-5,6-dicarboxylates. The nitrile sulfides, generated by thermal decarboxylation of 1,3,4-oxathiazol-2-ones, reacted with 1,4-naphthoquinone to afford 3-substituted naphtho[2,3-d] isothiazole-4,9-diones (17), together with nitriles as by-products. The corresponding reactions with 1,4-benzoquinone yielded regioisomeric mixtures of 2:1 adducts. The 1,2-benzisothiazole-5,6-dicarboxylates were synthesised by a sequence involving both nitrile sulfide and Diels-Alder cycloaddition reactions. Dimethyl 3-phenylisothiazole-4,5-dicarboxylate (34), prepared from benzonitrile sulfide and dimethyl acetylenedicarboxylate (DMAD), was converted into the 4,5-bis(dibromomethyl) analogue 37 via the bis(dihydroxymethyl) compound 35. Treatment of 37 with sodium iodide in the presence of DMAD afforded dimethyl 3-phenyl-1,2-benzisothiazole-5,6-dicarboxylate (30) via the isothiazole o-quinodimethane 32. ARKAT-USA, Inc.

Microwave-induced generation and reactions of nitrile sulfides: An improved method for the synthesis of isothiazoles and 1,2,4-thiadiazoles

The 1,3-dipolar cycloaddition reactions of nitrile sulfides, generated by microwave-assisted decarboxylation of 1,3,4-oxathiazol-2-ones, have been investigated. By this approach ethyl 1,2,4-thiadiazole-5-carboxylates 3 were prepared in good yield by cycloaddition of the nitrile sulfides to ethyl cyanoformate. Similarly, reaction of benzonitrile sulfide with dimethyl acetylenedicarboxylate (DMAD) afforded dimethyl 3-phenylisothiazole-4,5- dicarboxylate (5). In contrast, o-hydroxybenzonitrile sulfide, generated from the corresponding oxathiazolone 2d, reacted with DMAD to give methyl 4-oxo-4H-[1]benzopyrano[4,3-c]isothiazole-3-carboxylate (8) in high yield. A ca. 1:1 mixture of ethyl 3-phenylisothiazole-4- and 5-carboxylates (6,7) was formed from benzonitrile sulfide and ethyl propiolate. The corresponding reaction with diethyl fumarate gave diethyl trans-4,5-dihydro-3-phenylisothiazole-4,5- dicarboylate (10). 3-Arylisothiazoles, unsubstituted at both the 4- and 5-positions, were prepared from the reaction of 5-aryl-1,3,4-oxathiazolones with norbornadiene by a pathway involving cycloaddition of the nitrile sulfide to the norbornadiene, followed by retro-Diels-Alder extrusion of cyclopentadiene from the resulting isothiazoline cycloadduct 12. In summary, the use of microwave irradiation, rather than conventional heating methods, allows nitrile sulfide generation and reactions to be carried out in shorter times, with easier work-up and, in some cases, in higher yields.

ISOTHIAZOLE-PYRIDINE DERIVATIVES AS MODULATORS OF HIF (HYPOXIA INDUCIBLE FACTOR) ACTIVITY

The present invention relates to novel compounds according to Formula I or II, methods, and compositions capable of decreasing HIF hydroxylase enzyme activity, thereby increasing the stability and/or activity of hypoxia inducible factor (HIF). Formula (I) or (II).

PHOTOREACTION OF BENZENECARBOTHIOAMIDE WITH OLEFINS. SYNTHESES OF ISOTHIAZOLE DERIVATIVES AND PHENONES

Photoreaction of benzenecarbothioamide (1) in the presence of olefins gave isothiazole derivatives (10, 12, and 13) and 3,5-diphenyl-1,2,4-thiadiazole (11) under aerobic conditions, whereas under nitrogen atmosphere gave phenones (3 and 4).

Nitrile Sulphides. Part 3. Thermal Fragmentation of 1,3,4-Oxathiazoles: Formation of Nitrile Sulphides in a Retro-1,3-dipolar Cycloaddition Reaction

On thermolysis at ca. 160 gradC 1,3,4-oxathiazoles undergo retro-1,3-dipolar cycloaddition forming nitrile sulphides and carbonyl-containing fragments.The nitrile sulphides either decompose to sulphur and nitriles or are trapped as their 1,3-dipolar cycloadducts in the presence of dipolarophiles (dimethyl acetylenedicarboxylate, ethyl cyanoformate, benzonitrile, ethyl propiolate).Similar ratios (1.32, l.34, 1.33, 1.31) of 4- and 5-ethoxycarbonyl-3-(p-methoxyphenyl)isothiazole obtained from four sources of p-methoxybenzonitrile sulphide with ethyl propriolate provide strong evidence for product formation from a discrete intermediate nitrile sulphide rather than via direct interaction of precursor with dipolarophile. 2-Dichloromethylene-1,3,4-oxathiazoles, prepared by dehydrochlorination of 2-trichloromethyloxathiazoles, prepared by dehydrochlorination of 2-trichlorometyloxathiazoles, likewise fragment to nitrile sulphides, but attempts to trap dichloroketene were unsuccessful.

Synthesis and evaluation of furan, thiophene, and azole bis[(carbamoyloxy)methyl] derivatives as potential antineoplastic agents

A series of bis(hydroxymethyl)-substituted heterocycles were synthesized and converted to the corresponding bis(methylcarbamate) derivatives. The heterocyclic systems studied were based on 2-phenyl-3-methylfuran, 1-phenylpyrazole, 1-phenyl-5-methylpyrazole, 1-phenyl-5-methylthiopene, 1-phenyl-1,2,3-triazole, 3-phenylisoxazole, 3-phenylisothiazole, 2-phenylthiazole, and 2-phenyloxazole. None of the bis(carbamates) prepared was active against murine P388 lymphocytic leukemia. Pyrrole bis(carbamate), which exhibited antileukemic activity, also showed reactivity toward 4-(p-nitrobenzyl)pyridine while the inactive bis(carbamates) were unreactive in the 4-(p-nitrobenzyl)pyridine assay.

THE THERMAL FRAGMENTATION OF 1,3,4-DITHIAZOL-2-ONES

Thermal expulsion of carbon oxysulphide from 1,3,4-dithiazol-2-ones in the presence of DMAD affords nitrile sulphide-derived dimethyl isothiazole-4,5-dicarboxylates.

Synthesis, Thermal and Photochemical Reactions of New Mesoionic 1,3,2-Oxathiazolones

The synthesis and spectroscopic data of the new mesoionic 1,3,2-oxathiazolones 3b, c, e are described.As cyclic thiocarbonyl imine, 3e reacts with dimethyl acetylenedicarboxylate at 80 deg C with evolution of carbon dioxide to produce the 5-arylisothiazole derivative 6e (80percent).On the other hand, the visible light-induced fragmentation of 3e leads to a nitrile sulfide intermediate of type 10 which suffers unimolecular decay with formation of sulfur and the arylnitrile 11e or which can be partially trapped with dimethyl acethylenedicarboxylate to form the iosmeric 3-arylisothiazole derivative 13e (29-21percent).The analogous photochemical decay of 3c in the presence of dimethyl acetylenedicarboxylate proceeds with formation of the isothiazole derivative 13c besides sulfur and the nitrile 11c, whereas the nitrile sulfide 10b - photochemically generated from 3b - does not more react with formation of an isothiazole derivative.