cas 344-72-9, 2-AMINO-4-TRIFLUOROMETHYL-THIAZOLE-5-CARBOXYLIC ACID ETHYL ESTER

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Synthesis of 2-aminoethyl-5-carbethoxythiazoles utilizing a Michael-like addition strategy
Ethyl 4-(trifluoromethyl)-2-vinylthiazole-5-carboxylate was utilized as a precursor to ethyl 4-(trifluoromethyl)-2-(aminoethyl)thiazole-5-carboxylate analogs via Michael-like addition of various secondary amines. Reactions employed 1.2 equiv of amine, and the products were isolated by solvent removal and acid/base extraction. Use of primary amines was also investigated.
Boy, Kenneth M.,Guernon, Jason M.
p. 2251 - 2252
(2005)
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Optimization of Triarylpyridinone Inhibitors of the Main Protease of SARS-CoV-2 to Low-Nanomolar Antiviral Potency
Non-covalent inhibitors of the main protease (Mpro) of SARS-CoV-2 having a pyridinone core were previously reported with IC50 values as low as 0.018 μM for inhibition of enzymatic activity and EC50 values as low as 0.8 μM for inhibition of viral replication in Vero E6 cells. The series has now been further advanced by consideration of placement of substituted five-membered-ring heterocycles in the S4 pocket of Mpro and N-methylation of a uracil ring. Free energy perturbation calculations provided guidance on the choice of the heterocycles, and protein crystallography confirmed the desired S4 placement. Here we report inhibitors with EC50 values as low as 0.080 μM, while remdesivir yields values of 0.5-2 μM in side-by-side testing with infectious SARS-CoV-2. A key factor in the improvement is enhanced cell permeability, as reflected in PAMPA measurements. Compounds 19 and 21 are particularly promising as potential therapies for COVID-19, featuring IC50 values of 0.044-0.061 μM, EC50 values of ca. 0.1 μM, good aqueous solubility, and no cytotoxicity.
Zhang, Chun-Hui,Spasov, Krasimir A.,Reilly, Raquel A.,Hollander, Klarissa,Stone, Elizabeth A.,Ippolito, Joseph A.,Liosi, Maria-Elena,Deshmukh, Maya G.,Tirado-Rives, Julian,Zhang, Shuo,Liang, Zhuobin,Miller, Scott J.,Isaacs, Farren,Lindenbach, Brett D.,Anderson, Karen S.,Jorgensen, William L.
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p. 1325 - 1332
(2021/08/06)

Synthesis and Fungicidal Activity of Novel 2-Heteroatomthiazole-based Carboxanilides
A new series of 2-heteroatomthiazole-based carboxanilides (8) are prepared by reacting 2-heteroatomthiazole-based carboxylic acid chlorides with 2,6-dibromo-4-(trifluoromethoxy)aniline. The structures of all the newly synthesized compounds were supported by spectroscopic data NMR, MS, and elemental analysis, etc. Bioassay showed that the compounds exhibited potent fungicidal activities against Rhizoctonia solani, etc. Particularly, N-(2,6-dibromo-4-(trifluoromethoxy)phenyl)-2-methoxy-4-(trifluoromethyl)thiazole-5-carboxamide (8a-2) showed fungicidal potency which was comparable to that of Thifluzamide, the only commercialized thiazole carboxanilide fungicides of succinate dehydrogenase inhibitor (SDHI).
Liu, Aiping,Wang, Xiaoguang,Liu, Xingping,Li, Jianming,Chen, Haobin,Hu, Li,Yu, Wanqi,He, Lian,Liu, Weidong,Huang, Mingzhi
p. 1625 - 1629
(2017/03/27)

Synthesis and Insecticidal Activity of Novel Thiazole Acrylonitrile Derivatives
A series of novel thiazole acrylonitrile derivatives was designed and synthesized utilizing NC-510 as a precursor. Their structures were characterized by NMR spectrometry, MS, and elemental analysis. The results of bioassay indicated that some of these ti
Cao, Shengwen,Liu, Aiping,Liu, Weidong,Liu, Xingping,Ren, Yeguo,Pei, Hui,Huang, Lu,Zheng, Xi,Huang, Mingzhi,Wu, Daoxin
p. 3395 - 3402
(2017/11/21)

Synthesis and Biological Activity of Ethyl 4-Alkyl-2-(2-(substituted phenoxy)acetamido)thiazole-5-carboxylate
(Chemical Equation Presented) A series of novel ethyl 4-(methyl or trifluoromethyl)-2-(2-(substituted phenoxy)acetamido)thiazole-5-carboxylates 7a, 7b, 7c, 7d, 7e and 8f, 8g, 8h, 8i, 8j, 8k, 8l, 8m, 8n, 8o, 8p, 8q, 8r were synthesized, and their structures were confirmed by IR, 1H-NMR, MS spectra and elemental analysis. The results of preliminary bioassays show that some of the title compounds exhibit moderate to good herbicidal activities. Compared with the fluorine free compounds 7a, 7b, and 7e, the compounds bearing fluorine 8g, 8j, and 8q showed higher herbicidal activities with 70-100% inhibition against Capsella bursa-pastoris, Amaranthus restroflexus, and Eclipta prostrata at the dosage of 150 g/ha, which indicated that the trifluoromethyl on the thiazole ring was beneficial for the herbicidal activity. Furthermore, compounds 8f, 8g, 8h, 8i, 8j, 8k, 8l, 8m, 8n, 8o, 8p, 8q, 8r were tested for fungicidal activity against Pseudoperonospora cubensis at 500 μg/mL. Compounds 8f and 8q showed the best fungicidal activity with more than 80% inhibition.
Mo, Wenyan,Shi, Yanxia,He, Junbo,Li, Baoju,Peng, Hao,He, Hongwu
p. 183 - 187
(2016/02/10)

A kind of 3,4-dichloro-thiazole derivatives and process for their preparation and use
The invention provides 3,4-dichloro isothiazole derivatives, their preparation method and application. The invention relates to a heterocyclic compound containing 3,4-dichloro isothiazol, and the compound is represented by the following chemical structural general formula. The invention discloses the structural general formula of the compound, a synthetic method of the compound and applications of the compound as pesticide, bactericide, anti-plant virus agent, and plant activator, and a technology of mixing the compound with agriculturally acceptable auxiliary agents or synergists for preparing pesticide, bactericide, anti-plant virus agent, and plant activator. The invention further discloses the combined application of the compound and the commercial pesticide, bactericide, anti-plant virus agent, and plant activator in controlling diseases, insect pests, and virus diseases in agriculture, forestry and gardening, and a preparation method of the compound and the commercial pesticide, bactericide, anti-plant virus agent, and plant activator.
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(2016/10/08)

SUBSTITUTED BICYCLIC COMPOUNDS AS mPGES-1 INHIBITORS
The present disclosure is directed to compounds of formula (I), and pharmaceutically acceptable salts thereof, as mPGES-1 inhibitors. These compounds are inhibitors of the microsomal prostaglandin E synthase-1 (mPGES-1) enzyme and are therefore useful in the treatment of pain and/or inflammation from a variety of diseases or conditions, such as asthma, osteoarthritis, rheumatoid arthritis, acute or chronic pain and neurodegenerative diseases.
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(2014/10/29)

INHIBITORS OF DIACYLGLYCEROL ACYLTRANSFERASE
The present invention relates to novel heterocyclic compounds as diacylglycerol acyltransferase (“DGAT”) inhibitors, pharmaceutical compositions comprising the heterocyclic compounds and the use of the compounds for treating or preventing a cardiovascular disease, a metabolic disorder, obesity or an obesity-related disorder, diabetes, dyslipidemia, a diabetic complication, impaired glucose tolerance or impaired fasting glucose. An illustrative compound of the invention is shown below: formula (I).
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(2011/10/04)

THIAZOLE DERIVATIVES AS STEAROYL COA DESATURASE INHIBITORS
The present invention provides thiazole derivatives as Stearoyl CoA Desaturase (SCD) inhibitors. In particular, the compounds described herein are useful for treating or preventing diseases, conditions and/or disorders modulated by Stearoyl CoA Desaturase
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Page/Page column 29

(2010/04/03)

INHIBITORS OF DIACYLGLYCEROL ACYLTRANSFERASE
The present invention relates to novel heterocyclic compounds as diacylglycerol acyltransferase ("DGAT") inhibitors, pharmaceutical compositions comprising the heterocyclic compounds and the use of the compounds for treating or preventing a cardiovascular disease, a metabolic disorder, obesity or an obesity-related disorder, diabetes, dyslipidemia, a diabetic complication, impaired glucose tolerance or impaired fasting glucose. An illustrative compound of the invention is shown below.
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Page/Page column 169

(2010/07/10)

5-MEMBERED HETEROCYCLIC AMIDES AND RELATED COMPOUNDS
5-Membered heterocyclic amides and related compounds are provided, of the Formula: wherein variables are as described herein. Such compounds are ligands that may be used to modulate specific receptor activity in vivo or in vitro, and are particularly usef
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Page/Page column 97

(2009/03/07)

Studies of nonnucleoside HIV-1 reverse transcriptase inhibitors. Part 1: Design and synthesis of thiazolidenebenzenesulfonamides
A series of thiazolidenebenzenesulfonamides have been discovered as nonnucleoside reverse transcriptase inhibitors. Compound 17a exhibited the most potent inhibitory activity against the Y181C mutant reverse transcriptase (RT). The introduction of the 4-c
Masuda, Naoyuki,Yamamoto, Osamu,Fujii, Masahiro,Ohgami, Tetsuro,Fujiyasu, Jiro,Kontani, Toru,Moritomo, Ayako,Orita, Masaya,Kurihara, Hiroyuki,Koga, Hironobu,Nakahara, Hideaki,Kageyama, Shunji,Ohta, Mitsuaki,Inoue, Hiroshi,Hatta, Toshifumi,Suzuki, Hiroshi,Sudo, Kenji,Shimizu, Yasuaki,Kodama, Eiichi,Matsuoka, Masao,Fujiwara, Masatoshi,Yokota, Tomoyuki,Shigeta, Shiro,Baba, Masanori
p. 6171 - 6182
(2007/10/03)

Aminoalkyl thiazole derivatives as KCNQ modulators
Novel aminoalkylthiazole derivatives of Formula I are described which are openers of KCNQ potassium channels and are useful in the treatment of disorders responsive to the opening of the KCNQ potassium channels, including pain and migraine.
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Page/Page column 15

(2008/06/13)

2-aryl thiazole derivatives as KCNQ modulators
Novel 2-arylthiazole derivatives of Formula I are described which are openers of KCNQ potassium channels and are useful in the treatment of disorders that are responsive to the opening of the KCNQ potassium channels, including pain and migraine.
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Page 32

(2010/02/07)

SUBSTITUTED QUINAZOLINE DERIVATIVES AND THEIR USE AS INHIBITORS
The use of a compound of formula (I) 1 or a salt, ester or amide thereof; where X is O, or S, S(O) or S(O)2, or NR6 where R6 is hydrogen or C1-6 alkyl,; R5 is an optionally substituted 5-membered heteroaromatic ring, R1, R2 ,R3, R4 are independently selected from various specified moieties, in the preparation of a medicament for use in the inhibition of aurora 2 kinase. Certain compounds are novel and these, together with pharmaceutical compositions containing them are also described and claimed
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(2008/06/13)

Dehydroamino acids
Compounds of formula 1 and 1-1, wherein R1 is hydrogen, hydroxy, amino or halogen, R2 is hydrogen, hydroxy, or halogen and R3 is hydrogen (Formula 1) or R1 is hydrogen and R2 and R3 taken together with the ethenylene group connecting them form phenyl, pyrrole, pyrroline, oxopyrroline, pyrazole, triazole, or imidazole (Formula 1-1), A is R4 R5 are hydrogen, methyl, ethyl or halogen except that R4 r5 cannot both be hydrogen; and 1) B is hydrogen, or lower alkyl; or 2) B is where R6 R7 R8 and R9 are independently hydrogen, hydroxy, aminosulfonyl, halogen, lower alkoxy, cyano, amino, lower alkyl, lower alkyl amino, or nitro; or 3) B is where R10 is hydrogen, hydroxy, halogen, or lower alkyl and C is a five- or six- membered ring with 0 to 3 heteroatoms which heteroatoms are selected from nitrogen, oxygen, and sulfur, which ring may be unsubstituted or mono- or di- substituted with lower alkyl, cycloalkyl, amino, or substituted amino; 4) B is where X and Y are independently methylene or nitrogen; or 5) B is where at leat one of T, U, V, or W is nitrogen, and any of T, U, V or W which is carbon may be substituted with lower alkyl, lower alkyl amino, lower alkoxy, hydroxy, aminosulfonyl, halogen, cyano, amino, or nitro; or 6) B is where Y is carbon or nitrogen; or 7) B is a five-membered aromatic ring with 1 to 3 heteratoms selected from nitrogen, oxygen, and sulfur which ring may be unsubstituted or mono- or di-substituted with lower alkyl, cycloalky, trifluoroloweralkyl, amino, halogen, substituted amino, or which ring may be fused with a 5 or 6 membered aromatic ring containing 0 to 3 heteroatoms which heteroatoms are selected from nitrogen, oxygen, and sulfur; and pharmaceutically acceptable salts thereof, and related prodrugs, pharmaceutical compositions and methods of treatment, which compounds are useful for treating psoriasis.
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(2008/06/13)

4-Chloro-5H-1,2,3-dithiazol-5-one: A good α-thiocyanating agent for α,β-unsaturated β-amino esters
Treatment of 4-chloro-5H- 1,2,3-dithiazol-5-one with 3-alkyl (or aryl)- 3-amino-2-propenoate esters in DMSO at 120°C gave the corresponding 2- thiocyanated esters 4 (major) and 5-alkoxycarbonyl-4-alkyl (or aryl)-4- thiazolin-2-ones 5 (minor), whereas the
Park, Young Seok,Kim, Kyongtae
p. 6439 - 6442
(2007/10/03)

Synthesis of Trifluoromethylthiazoles and Their Application to Azo Dyes
3-Bromo-1,1,1-trifluoropropan-2-one (2) reacted with thiourea and N-monosubstituted thiourea to give the corresponding 4-trifluoromethylthiazoles, respectively.In the reactions with N,N'-diphenylthiourea and thioamides, the considerably stable intermediat
Tanaka, Kiyoshi,Nomura, Kazuto,Oda, Hitoshi,Yoshida, Shouhei,Mitsuhashi, Keiryo
p. 907 - 911
(2007/10/02)

Syntheses and Reactions of 2-Halo-5-thiazolecarboxylates
A variety of 2-halo-5-thiazolecarboxylates was prepared from substituted-3-aminoacrylates and 3-ketoesters.Selective reduction of 2-chloro-5-thiazolecarboxylates 4a, 4i and 4j with sodium borohydride in ethanol provided the corresponding 2-halo-5-thiazolemethanols 27 - 29.Nucleophilic displacement on methyl methanesulfonate (32c) occured selectivity at the 5-substituent to provide 2-chloro-4-(trifluoromethyl)-5-(heteroatom-substituted methyl)thiazoles 32d-f.
Lee, Len F.,Schleppnik, Francis M.,Howe, Robert K.
p. 1621 - 1630
(2007/10/02)