366-50-7

Upstream product

• 653-22-5 1-Acetylamino-2,3,4,5,6-pentafluorobenzen 
• 367-34-0 2,4,5-trifluoroaniline 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 
• 2105-61-5 1,2,4-trifluoro-5-nitrobenzene 

Downstream Products

• 388-11-4 N-(3,4,6-trifluoro-2-nitrophenyl)acetamide 
• 769-34-6 1,2-dichloro-3,5,6-trifluorobenzene 
• 66684-57-9 1,2,5-trifluoro-3-nitrobenzene 
• 367-34-0 2,4,5-trifluoroaniline 
• 131105-93-6 4,5-difluoro-2-aminothiophenol 
• 170881-41-1 5,6-difluoro-2-methylbenzo[d]thiazole 
• 906081-31-0 2,3-diamino-4,6-difluoro-phenol 
• 361-39-7 3,4,6-trifluoro-2-nitro-aniline 

Relevant academic research and scientific papers

TRANSGLUTAMINASE 2 (TG2) INHIBITORS

Described herein are compounds and pharmaceutical compositions containing such compounds which inhibit transglutaminase 2 (TG2). Also described herein are methods for using such TG2 inhibitors, alone or in combination with other compounds, for treating diseases or conditions that would benefit from TG2 inhibition.

Interaction of polyfluorinated 2-chloroquinolines with ammonia

We have studied the interaction of polyfluorinated (in the benzene moiety) 2-chloroquinolines with liquid and aqueous ammonia as an approach to the synthesis of halogen-containing aminoquinolines. 5,7-Difluoro-, 5,6,8-trifluoro-, and 5,7,8-trifluoro-2-chloroquinolines mostly form products of substitution of the Cl atom, whereas 5,7-difluoro-2,6-dichloroquinoline, 5,6,7,8-tetrafluoro-, and 6,7-difluoro-2-chloroquinolines yield products of substitution of an F atom at various positions. The replacement of liquid ammonia with aqueous causes an increase in the proportion of the products of aminodechlorination relative to the products of aminodefluorination. For 2-chloro-6,8-difluoroquinoline this replacement leads to 2-amino-6,8-difluoroquinoline as the main product instead of the 8-amino-derivative. Activation energy values estimated by DFT calculations for the reactions in question agree with the reaction regioselectivity observed experimentally.

MOLECULAR AND POLYMERIC SEMICONDUCTORS AND RELATED DEVICES

The present invention relates to new semiconducting compounds having at least one optionally substituted benzo[d][1,2,3]thiadiazole moiety. The compounds disclosed herein can exhibit high carrier mobility and/or efficient light absorption/emission charact

Benzo[d][1,2,3]thiadiazole (isoBT): Synthesis, Structural Analysis, and Implementation in Semiconducting Polymers

Benzo[d][2,1,3]thiadiazole (BT) is a markedly electron-deficient heterocycle widely employed in the realization of organic semiconductors for applications spanning transistors, solar cells, photodetectors, and thermoelectrics. In this contribution, we imp

Synthesis of polyfluorinated 4-phenyl-3,4-dihydroquinolin-2-ones and quinolin-2-ones via superacidic activation of N-(polyfluorophenyl)cinnamamides

The cyclization reactions of a series of polyfluorocinnamanilides in triflic acid (CF3SO3H) yield 4-phenyl-3,4-dihydroquinolin-2-ones, which include a polyfluorinated benzene moiety as a part of the quinoline scaffold. These compounds undergo dehydrophenylation in the presence of AlCl3 to give the corresponding polyfluoroquinolin-2-ones which are converted into polyfluorinated 2-chloroquinolines on treatment with POCl3. A mechanism for the cyclization reaction presuming the intermediacy of a superelectrophilic O,C-diprotonated form of the starting material is suggested.

N-acetylation as a means to activate polyfluoroarylamines for selective ortho-hydrodefluorination by zinc in aqueous ammonia: A concise route to polyfluorobenzo azaheterocycles

N-Acetylation of polyfluoroarylamines is proposed as a means to remove the amino group blocking effect of their hydrodefluorination by zinc in aqueous ammonia. With pentafluoroacetanilide, the Zn ion specific effect has been demonstrated to be responsible for ortho hydrodefluorination. This regiochemistry is accompanied by the removal of a fluorine atom from the para position, which occurs predominantly in the initial phase of the process in the absence of deliberately added zinc salt. The CuCl2 additive has been found to accelerate the reaction and to propel it to double defluorination. Quantum chemical calculations suggest a diminished electron affinity of pentafluoroaniline, which is responsible for its inertness in relation to the hydrodefluorination reaction. The pentafluoroaniline radical anion, which essentially has a nonplanar structure, is prone to easy fragmentation to give an aminotetrafluorophenyl radical. For pentafluoroacetanilide, CVA experiments and quantum chemical calculations predict that the pentafluorophenyl moiety serves as the electron receptor and that the acetamido group is twisted out of coplanarity with the benzene ring; thus, together with the electron-withdrawing effect of the acetyl group, the amino group blocking effect is suppressed. On this ground, the selective ortho hydrodefluorination of polyfluoroacetanilides is developed as an important protocol for the expeditious and general synthesis of polyfluorobenzo azaheterocycles via readily accessible polyfluoroarylamines from base polyfluoroarenes. Its applicability has been illustrated by preparing quinolines that possess a polyfluorinated benzene moiety by the Skraup synthesis utilizing crude polyfluoroacetanilide hydrodefluorination products as starting materials. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Identification of metabolites of the tryptase inhibitor CRA-9249: Observation of a metabolite derived from an unexpected hydroxylation pathway

The metabolites of the tryptase inhibitor CRA-9249 were identified after exposure to liver microsomes. CRA-9249 was found to be degraded rapidly in liver microsomes from rabbit, dog, cynomolgus monkey, and human, and less rapidly in microsomes from rat. T

Discovery of 3-[(4,5,7-trifluorobenzothiazol-2-yl)methyl]indole-N-acetic acid (lidorestat) and congeners as highly potent and selective inhibitors of aldose reductase for treatment of chronic diabetic complications

Recent efforts to identify treatments for chronic diabetic complications have resulted in the discovery of a novel series of highly potent and selective 3-[(benzothiazol-2-yl)methyl]indole-N-alkanoic acid aldose reductase inhibitors. The lead candidate, 3-[(4,5,7-trifluorobenzothiazol-2-yl)methyl]indole-N-acetic acid (lidorestat, 9) inhibits aldose reductase with an IC50 of 5 nM, while being 5400 times less active against aldehyde reductase, a related enzyme involved in the detoxification of reactive aldehydes. It lowers nerve and lens sorbitol levels with ED50's of 1.9 and 4.5 mg/kg/d po, respectively, in the 5-day STZ-induced diabetic rat model. In a 3-month diabetic intervention model (1 month of diabetes followed by 2 months of drug treatment at 5 mg/kg/d po), it normalizes polyols and reduces the motor nerve conduction velocity deficit by 59% relative to diabetic controls. It has a favorable pharmacokinetic profile (F, 82%; t1/2, 5.6 h; Vd, 0.694 L/kg) with good drug penetration in target tissues (Cmax in sciatic nerve and eye are 2.36 and 1.45 μg equiv/g, respectively, when dosed with [14C] lidorestat at 10 mg/kg po).

A new approach to polyfluoroaromatic amines with an unsubstituted position ortho to the amino group

N-acetyl derivatives of polyfluoroaromatic amines have been found to be highly selectively defluorinated by zinc in aqueous ammonia at the position ortho to the acetamido group thus affording a new approach to potential building blocks for the synthesis o