cas 30748-47-1, 2-Amino-4-methyl-5-acetylthiazole

Articles about 30748-47-1Total 32 be found

Article title
Article abstract
Author
Journal number and time
Download

Antiviral drugs. XVIII: 2-Aminothiazoles by cleavage of the S-S-bond of disulfidodicarbamidine
-
Kreutzberger,Schimmelpfennig
p. 385 - 391
(1981)
Read Online

Synthesis and application of 2-N-(thiazol-2-yl)benzo/naphtho [1,2-d]-1,2,3-triazoles
The synthesis of a series of bright, intensely fluorescent brighteners bused on 2-N-(thiazol-2-yl)benzo/naphtho [1,2-d]-1,2,3-triazoles is described. The absorption - emission spectra of the fluorescent brighteners were recorded and their dyeing properties were studied.
Rangnekar, Dinesh W.,Kazemi, Gadhir J.,Malanker, Jayesh V.,Ramamurthy, Rajesh
p. 185 - 190
(1998)
Read Online

N-(5-acetyl-4-methylthiazol-2-yl)arylamide derivatives as multi-target-directed ligands: design, synthesis, biochemical evaluation and computational analysis
In the present study, we are reporting the synthesis of a total eight derivatives of N-(5-acetyl-4-methylthiazol-2-yl) Arylamide derivatives (3a-h). The products obtained in good to excellent yield represents drug-like molecules with a well-developed structure-activity relationship. All the synthesized compounds were further subjected to chemical characterization (NMR, FTIR and elemental analysis) and further tested for biological activities (antioxidant, antibacterial, antifungal and α-glucosidase). The anti-oxidant properties of compound 3h (IC50 ± SEM = 141.9 ± 1.12?μg/mL) were found maximum in comparison to the rest of the derivatives. The antibacterial results showed the compounds 3d and 3h as a significant bacterial inhibitor. The significant fungicidal activity was observed by compound 3a with the zone of inhibition up to 24 mm which in comparison with the results of positive control (Terbinafine). When the effect was observed on α-glucosidase activity, the highest enzyme inhibition activity was observed by 3h (IC50 ± SEM 134.4 ± 1.01?μg/mL) followed by 3c (IC50 ± SEM = 157.3 ± 1.11?μg/mL). The results were further supported by molecular docking studies and the chemical stability of the derivatives was also performed by density functional theory (DFTs) calculations. The data revealed that most of the derivatives are multi-target ligands and can be used as lead molecules for the synthesis of derivatives for their further evaluation at molecular targets for the treatment of specific diseases. Graphical abstract: [Figure not available: see fulltext.] Synopsis This article reports the synthesis of a total of eight derivatives of N-(5-acetyl-4-methylthiazol-2-yl) Arylamide derivatives. The products obtained in good to excellent yield represents drug-like molecules with a well-developed structure-activity relationship.
Channar, Kashif Ali,Channar, Pervaiz Ali,Ejaz, Syeda Abida,Indher, Hafiz Abdul Bari,Ismail, Hammad,Mahmood, Hafiz Mohammad Kashif,Rafiq, Mamoona,Saeed, Aamer,Saeed, Amna,Saeed, Shomaila,Ujan, Rabail
(2022/01/19)

Synthesis, Characterization, Crystal Structure and Biological Study of Carboxamides Obtained from 2-Aminothiazole Derivatives
Abstract: Two series of novel thiazolylcarboxamide derivatives were synthesized by the reaction of ethyl 2-amino-4-methylthiazole-5-carboxylate or 1-(2-amino-4-methylthiazol-5-yl)ethan-1-one with four substituted carbonyl chlorides at 0?°C in excellent yi
Wazalwar, Sachin S.,Banpurkar, Anita R.,Perdih, Franc
p. 319 - 329
(2019/07/29)

Design, synthesis, antitumor activity and theoretical calculation of novel PI3Ka inhibitors
PI3Kα has been identified as an ideal target to treat with PIK3CA gene mutation disease, including drugs such as Alpelisib and Copanlisib. Five purine analogues and four thiazole analogues were designed and synthesized. Their enzymatic activity against PI3Ka/β/γ/δ were tested, respectively. All compounds showed excellent selectivity in modulating PI3Ka activity, and parts of the compounds showed good inhibition. Meanwhile, we used Autodock 4.2 to explore the binding mode of the most potential compound Tg with the target protein. In addition, DFT was used to calculate the HOMO-LUMO maps of the compounds Tf, Tg and positive control. This paper will provide some useful information for further drug design of PI3Kα inhibitors.
Guo, Hui,Jin, Ru-Yi,Li, Zhi,Long, Xu,Tang, Tian,Tang, Yu-Ping,Xie, Hong-Lei,Yan, Hao,Zhou, Jing,Zhou, Sha,Zuo, Zheng-Yu
(2020/03/18)

5 - (3 - Phenyl-acryloyl) thiazole derivative and its preparation method and application (by machine translation)
The present invention is shown in formula I 5 - (3 - phenyl-acryloyl) thiazole derivatives and their pharmaceutically acceptable salt, pharmaceutical composition and thereof in the preparation of influenza virus neuraminidase inhibitors in the application. Wherein R is selected from: methyl, ethyl, C3 - C4 Straight-chain or C3 - C4 Branched alkyl; R1 Is selected from: hydrogen, 2 - nitro, 3 - nitro, 4 - nitro, 2 - amino, 3 - amino, 4 - amino, 2 - methylamino, 3 - methylamino, 4 - methylamino, 2 - dimethylamino, 3 - dimethylamino, 4 - dimethylamino, 2 - methoxy, 3 - methoxy, 4 - methoxy, 2 - ethoxy, 3 - ethoxy, 4 - ethoxy, 2 - hydroxy, 3 - hydroxy, 4 - hydroxy, 2, 3 - dihydroxy, 2, 4 - dihydroxy, 2, 5 - dihydroxy, 3, 4 - dihydroxy, 3, 5 - dihydroxy, 2 - hydroxy - 3 - methoxy, 3 - hydroxy - 4 - methoxy, 4 - hydroxy - 3 - methoxy, 4 - hydroxy - 3 - ethoxy, 3, 4, 5 - trimethoxy or 4 - hydroxy - 3, 5 - dimethoxy; R2 Is selected from: hydrogen, C1 - C2 Alkyl, C3 - C4 Straight-chain or C3 - C4 Branched alkyl, trifluoromethyl or chloro C1 - C4 Straight-chain alkyl. (by machine translation)
-
(2018/10/02)

Novel indole-thiazolidinone conjugates: Design, synthesis and whole-cell phenotypic evaluation as a novel class of antimicrobial agents
In connection with our research program on the development of novel anti-tubercular candidates, herein we report the design and synthesis of two different sets of indole-thiazolidinone conjugates (8a,b; 11a-d) and (14a-k; 15a-h). The target compounds were evaluated for their in vitro antibacterial and antifungal activities against selected human pathogens viz. Staphylococcus aureus (Gram positiveve), Pseudomonas aeruginosa, Escherichia coli (Gram negative), Mycobacterium tuberculosis (Acid-fast bacteria), Aspergillus fumigates and Candida albicans (fungi). Moreover, eukaryotic cell-toxicity was tested via an integrated ex vivo drug screening model in order to evaluate the selective therapeutic index (SI) towards antimicrobial activity when microbes are growing inside primary immune cells. Also, the cytotoxicity towards a panel of cancer cell lines and human lung fibroblast normal cell line, WI-38 cells, was explored to assure their safety. Compound 15b emerged as a hit in this study with potent broad spectrum antibacterial (MIC: 0.39–0.98 μg/mL) and antifungal (MIC: 0.49–0.98 μg/mL) activities, in addition to its ability to kill mycobacteria M. aurum inside an infected macrophage model with good therapeutic window. Moreover, compound 15b displayed promising activity towards resistant bacteria strains MRSA and VRE with MIC values equal 3.90 and 7.81 μg/mL, respectively. These results suggest compound 15b as a new therapeutic lead with good selectivity for further optimization and development.
Abo-Ashour, Mahmoud F.,Eldehna, Wagdy M.,George, Riham F.,Abdel-Aziz, Marwa M.,Elaasser, Mahmoud M.,Abdel Gawad, Nagwa M.,Gupta, Antima,Bhakta, Sanjib,Abou-Seri, Sahar M.
p. 49 - 60
(2018/10/20)

TBHP/AIBN-Mediated Synthesis of 2-Amino-thioazoles from Active Methylene Ketones and Thiourea under Metal-free Conditions
A new oxidative system of tert-butyl hydroperoxide (TBHP)/azodiisobutyronitrile (AIBN) has been used for the first time for a convenient, metal-free synthesis of substituted 2-aminothioazoles from active methylene ketone derivatives and thiourea. The reaction is postulated to proceed via an oxidative cyclization initiated by a radical process and followed by a condensation reaction.
Sun, Jiyun,Ge, Huaibin,Zhen, Xiaohua,An, Xuechan,Zhang, Guangtao,Zhang-Negrerie, Daisy,Du, Yunfei,Zhao, Kang
p. 2107 - 2114
(2018/03/26)

Nitrogenous condensed heterocyclic compound as well as preparation method, intermediate, composition and application thereof
The invention discloses a nitrogenous condensed heterocyclic compound as well as a preparation method, an intermediate, a composition and application thereof. The compound disclosed by the invention has high inhibition activity for different subtypes of CDK (Cyclin-Dependent Kinase) at a molecular level, has good inhibition activity on breast cancer cells at a cell level, has a remarkable proliferation inhibition function on tumor cells related to cyclin-dependent kinase activity at an animal level, is good in liver microsome stability upon human beings, mice, and the like, is good in in-vivoabsorption in mice and rats, is high in bioavailability and is good in druggability.
-
Paragraph 0315; 0316; 0317; 0318

(2018/11/22)

MANNOSE DERIVATIVES USEFUL FOR TREATING PATHOLOGIES ASSOCIATED WITH ADHERENT E. COLI
The present invention relates to mannose derivatives of formula (I): wherein R1 represents H, CO-(C1-C6)-alkyl or CO-alkylaryl, Y represents a single bond, CH2, O, NR3, S, A represents O, NH or S, X represents H and X' represents OH or X and X' taken together with the carbon atom bearing them form a CO group, R2 represents H, a linear or branched (C1-C6 )-alkyl or CF3, R3 represents H, a C1-C6 alkyl, a CO-(C1-C6 )-alkyl, CF3 or COCF3, and R is as described in claim 1. The mannose derivatives of formulae (I) are useful for treating pathologies associated with the presence of adherent Escherichia coli (AEC), in particular inflammatory bowel diseases (IBD), such as Crohn's disease and ulcerative colitis; a urinary tract infection, in particular painful bladder syndrome and cystitis, more particularly interstitial cystitis; irritable bowel syndrome; metabolic diseases such as metabolic obesity, diabetes, hypercholesterolemia; autoimmune inflammatory diseases; and colorectal cancer, in particular colon cancer.
-
Page/Page column 70

(2017/02/28)

Microwave-assisted green synthesis of new imidazo[2,1-b]thiazole derivatives and their antimicrobial, antimalarial, and antitubercular activities
Abstract: We have synthesized some imidazo[2,1-b]thiazole derivatives by reaction of 1-(2-amino-4-methylthiazol-5-yl)ethanone or ethyl 2-amino-4-methylthiazole-5-carboxylate with α-bromo aralkyl ketones (phenacyl bromides) in presence of polyethylene glycol-400 (PEG-400) as efficient, inexpensive, biodegradable, and green reaction medium and catalyst (dual nature) under Microwave Irradiation (MWI) at 300?W as well as under thermal heating at 90?°C. Moreover, we also synthesized 1-(2-amino-4-methylthiazol-5-yl)ethanone and ethyl 2-amino-4-methylthiazole-5-carboxylate by one-pot reaction of acetyl acetone/ethyl acetoacetate with N-bromosuccinimide (NBS) and thiourea in presence of PEG-400 under microwave irradiation at 180?W. All synthesized compounds were screened for antimicrobial and antimalarial activities. All compounds were found to show good to excellent antibacterial activity, and some analogs exhibited good antimalarial activity.
Vekariya, Rajesh H.,Patel, Kinjal D.,Vekariya, Mayur K.,Prajapati, Neelam P.,Rajani, Dhanji P.,Rajani, Smita D.,Patel, Hitesh D.
p. 6207 - 6231
(2017/10/05)

C[sbnd]N bond formation in alicyclic and heterocyclic compounds by amine-modified nanoclay
In the current protocol, amine functionalized montmorillonite K10 nanoclay (NH2-MMT) was applied to catalyze the formation of C[sbnd]N bonds in the synthesis of azines and 2-aminothiazoles at room temperature. In comparison with the current methods of C[sbnd]N bond formation, this approach displays specific advantages include atom economy, clean conversion, design for energy efficiency, the use of nontoxic and heterogeneous catalyst, higher purity and yields, safer solvent and reagents for this organic transformation.
Zarnegar, Zohre,Alizadeh, Roghayeh,Ahmadzadeh, Majid,Safari, Javad
p. 58 - 65
(2017/05/12)

Discovery of Multitarget Agents Active as Broad-Spectrum Antivirals and Correctors of Cystic Fibrosis Transmembrane Conductance Regulator for Associated Pulmonary Diseases
Enteroviruses (EVs) are among the most frequent infectious agents in humans worldwide and represent the leading cause of upper respiratory tract infections. No drugs for the treatment of EV infections are currently available. Recent studies have also linked EV infection with pulmonary exacerbations, especially in cystic fibrosis (CF) patients, and the importance of this link is probably underestimated. The aim of this work was to develop a new class of multitarget agents active both as broad-spectrum antivirals and as correctors of the F508del-cystic fibrosis transmembrane conductance regulator (CFTR) folding defect responsible for >90% of CF cases. We report herein the discovery of the first small molecules able to simultaneously act as correctors of the F508del-CFTR folding defect and as broad-spectrum antivirals against a panel of EVs representative of all major species.
Tassini, Sabrina,Sun, Liang,Lanko, Kristina,Crespan, Emmanuele,Langron, Emily,Falchi, Federico,Kissova, Miroslava,Armijos-Rivera, Jorge I.,Delang, Leen,Mirabelli, Carmen,Neyts, Johan,Pieroni, Marco,Cavalli, Andrea,Costantino, Gabriele,Maga, Giovanni,Vergani, Paola,Leyssen, Pieter,Radi, Marco
p. 1400 - 1416
(2017/03/08)

Synthesis, characterization and cholinesterase inhibition studies of new arylidene aminothiazolylethanone derivatives
Background: Alzheimer's disease is caused by the destruction or loss of cholinergic cells that produce or use ACh in the brain, thereby reducing the availability of enzyme to other cells. The major treatment strategy for AD is to decrease the level of cholinesterase in the brain. Objective: The aim of this study was to describe the effect of novel series of thiazole derivatives i.e. arylidene aminothiazolylethanones (3a-h) as cholinesterase inhibitors (CEIs). Method: A novel series of thiazole derivatives i.e. arylidene aminothiazolylethanones (3a-h) was synthesized by treating 3-chloropentane-2,4-dione (1) with urea followed by reaction with suitably substituted benzaldehydes. Structural confirmation of all the synthesized compounds was carried out by spectroscopic techniques (FTIR, 1H and 13CNMR) and elemental analysis. Furthermore, these derivatives were subjected to biological evaluation as potential inhibitors of cholinesterases i.e. acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). Results: In all synthesized compounds except two compounds i.e. 3a and 3f, all compounds were identified as selective inhibitors of AChE. Compound 3a exhibited potent inhibitory values against AChE (IC50± SEM = 1.78±0.11 μM), exhibiting ≈7 times greater selectivity for AChE over BChE. Kinetics studies were performed to find out the mechanism of inhibition against respective enzyme. In addition, molecular docking studies of most potent inhibitors were also carried out to determine the binding interactions with AChE and BChE, respectively. Conclusion: In this study, novel thiazole derivatives i.e. arylidene aminothiazolylethanones were successfully synthesized, characterized and further screened for threir potential as cholinesterase inhibitors. All compounds were found as potent selective inhibitors of AChE except two compounds which exhibited dual inhibitory activities but both of these compounds were highly selective toward AChE as compared to BChE.
Channar, Pervaiz A.,Saeed, Aamer,Larik, Fayaz A.,Shabir, Ghulam,Shah, Muhammad S.,Khan, Shafi U.,Iqbal, Jamshed
p. 648 - 653
(2018/02/02)

Dual Inhibition of Mnk2 and FLT3 for potential treatment of acute myeloid leukaemia
The discovery of novel anti-AML therapeutic agents is urgently needed, but the complex heterogeneity of the disease has so far hampered the development of a curative treatment. FLT3 inhibitors have shown therapeutic potential in clinical trials; but a monotherapy regimen has been associated with resistance mediated by the activation of parallel signalling circuitry, including MAPK and mTOR. Therefore, inhibiting a nexus of the two signalling pathways along with inhibition of FLT3 might be advantageous. Herein, we propose that a dual inhibition of FLT3 and Mnk would provide a better clinical option for AML patients compared to targeting FLT3 alone. Thus, a series of N-phenyl-4-(thiazol-5-yl)pyrimidin-2-amines and 4-(indol-3-yl)-N-phenylpyrimidin-2-amines were prepared. Potent Mnk2 inhibitors, FLT3 inhibitors, and dual inhibitors of Mnk2 and FLT3 were identified and their anti-proliferative activities assessed against MV4-11 AML cell lines. Dual inhibition of FLT3 and Mnk2 caused the increased apoptotic cell death of MV4-11 cells compared to inhibition of FLT3 or Mnk2 alone.
Diab, Sarah,Abdelaziz, Ahmad M.,Li, Peng,Teo, Theodosia,Basnet, Sunita K.C.,Noll, Ben,Rahaman, Muhammed H.,Lu, Jingfeng,Hou, Jinqiang,Yu, Mingfeng,Le, Bich T.,Albrecht, Hugo,Milne, Robert W.,Wang, Shudong
supporting information
p. 762 - 772
(2017/09/02)

Substituted N-Phenyl-5-(2-(phenylamino)thiazol-4-yl)isoxazole-3-carboxamides Are Valuable Antitubercular Candidates that Evade Innate Efflux Machinery
Tuberculosis remains one of the deadliest infectious diseases in the world, and the increased number of multidrug-resistant and extremely drug-resistant strains is a significant reason for concern. This makes the discovery of novel antitubercular agents a cogent priority. We have previously addressed this need by reporting a series of substituted 2-aminothiazoles capable to inhibit the growth of actively replicating, nonreplicating persistent, and resistant Mycobacterium tuberculosis strains. Clues from the structure-activity relationships lining up the antitubercular activity were exploited for the rational design of improved analogues. Two compounds, namely N-phenyl-5-(2-(p-tolylamino)thiazol-4-yl)isoxazole-3-carboxamide 7a and N-(pyridin-2-yl)-5-(2-(p-tolylamino)thiazol-4-yl)isoxazole-3-carboxamide 8a, were found to show high inhibitory activity toward susceptible M. tuberculosis strains, with an MIC90 of 0.125-0.25 μg/mL (0.33-0.66 μM) and 0.06-0.125 μg/mL (0.16-0.32 μM), respectively. Moreover, they maintained good activity also toward resistant strains, and they were selective over other bacterial species and eukaryotic cells, metabolically stable, and apparently not susceptible to the action of efflux pumps.
Azzali, Elisa,Machado, Diana,Kaushik, Amit,Vacondio, Federica,Flisi, Sara,Cabassi, Clotilde Silvia,Lamichhane, Gyanu,Viveiros, Miguel,Costantino, Gabriele,Pieroni, Marco
supporting information
p. 7108 - 7122
(2017/09/07)

Synthesis of 2-aminothiazoles from methylcarbonyl compounds using a Fe3O4 nanoparticle-: N -halo reagent catalytic system
An efficient protocol is developed for the synthesis of 2-aminothiazoles from unfunctionalized methylcarbonyl compounds using Fe3O4 nanoparticle-N-halo reagent catalytic systems. 1,3-dichloro-5,5-dimethylhydantoin (DCDMH), N-bromosuccinimide (NBS) and N-iodosuccinimide (NIS) as N-halo reagents were explored and the best results were obtained for DCDMH. Fe3O4 nanoparticle-DCDMH as an active, reusable, excellent, highly stable magnetic catalyst was used in this process. Advantages of this efficient method include greener and cleaner conditions, shorter reaction time, excellent yield of products, easy separation using a simple external magnetic field, low cost and operational simplicity.
Sadeghi, Masoud,Safari, Javad,Zarnegar, Zohre
p. 64749 - 64755
(2016/07/21)

Magnetic carbon nanotube-supported imidazolium cation-based ionic liquid as a highly stable nanocatalyst for the synthesis of 2-aminothiazoles
Magnetic carbon nanotube-supported imidazolium ionic liquid (CNT-Fe3O4-IL) was synthesized and investigated using various characterization techniques, including Fourier transform infrared and Raman spectroscopies, X-ray diffraction, vibrating sample magnetometry, scanning and transmission electron microscopies, and thermogravimetric and differential thermal analyses. In order to synthesize the CNT-Fe3O4-IL nanocomposites, Fe3O4-decorated multi-walled CNTs were modified with 1-methyl-3-(3-trimethoxysilylpropyl)-1H-imidazol-3-ium chloride. This catalytic system was found to be a highly stable, active, reusable and solid-phase catalyst for the synthesis of 2-aminothiazoles via the one-pot reaction of ketone, thiourea and N-bromosuccinimide under mild conditions. Immobilized magnetic ionic liquid catalysis combines the advantages of ionic liquid media with magnetic solid support nanomaterials which enables the application of nanotechnology and green chemistry in chemical processes. Copyright
Zarnegar, Zohre,Safari, Javad
p. 1043 - 1049
(2016/11/23)

Nanochitosan: A biopolymer catalytic system for the synthesis of 2-aminothiazoles
A convenient and efficient method is described for the synthesis of 2-aminothiazoles by one-pot reaction of ketone and thiourea using chitosan nanoparticles under mild condition. Nanochitosan was used as a biodegradable and green catalyst for this reaction in satisfactory yields. The attractive advantages of the present process include easy isolation of products, milder and cleaner conditions, higher purity and yields and easier work-up procedure.
Safari, Javad,Abedi-Jazini, Zahra,Zarnegar, Zohre,Sadeghi, Masoud
p. 108 - 112
(2016/02/05)

Convenient and simple synthesis of 2-aminothiazoles by the reaction of α-halo ketone carbonyls with ammonium thiocyanate in the presence of N-methylimidazole
Substituted 2-aminothiazole derivatives were obtained as a result of N-methylimidazole catalyzed cyclization of α-halo ketone carbonyls with ammonium thiocyanate in water-alcoholic media. The generality of the method has been demonstrated by screening a series of aromatic/heteroaromatic/aliphatic α-halo ketones, α-halo β-diketones, and α-halo β-ketoesters. The developed method is simple, mild, and general route for the preparation of diversely functionalized 2-aminothiazoles in good to moderate yields from readily available starting materials.
Meshram,Thakur, Pramod B.,Madhu Babu,Bangade, Vikas M.
p. 5265 - 5269
(2012/10/30)

Fluorinated DF508-CFTR correctors and potentiators for PET imaging
19F-modified bithiazole correctors and phenylglycine potentiators of the DF508-CFTR chloride channel were synthesized and their function assayed in cells expressing human DF508-CFTR and a halide-sensitive fluorescent protein. Fluorine was incorporated into each scaffold using prosthetic groups for future biodistribution imaging studies using positron emission tomography (PET). The DF508-CFTR corrector and potentiator potencies of the fluorinated analogs were comparable to or better than those of the original compounds.
Davison, Holly R.,Solano, Danielle M.,Phuan, Puay-Wah,Verkman,Kurth, Mark J.
scheme or table
p. 1602 - 1605
(2012/04/10)

Click-based synthesis of triazolobithiazole Δf508-CFTR correctors for cystic fibrosis
Copper catalyzed azide-alkyne cycloaddition (CuAAC) chemistry is reported for the construction of previously unknown 5-(1H-1,2,3-triazol-1-yl)-4,5′- bithiazoles from 2-bromo-1-(thiazol-5-yl)ethanones. These novel triazolobithiazoles are shown to have cyst
Donald, Michael B.,Rodriguez, Kevin X.,Shay, Hannah,Phuan, Puay-Wah,Verkman,Kurth, Mark J.
p. 5247 - 5253
(2012/11/07)

Piperidine-mediated synthesis of thiazolyl chalcones and their derivatives as potent antimicrobial agents
A series of new thiazolyl chalcones, 1-[2-amino-4-methyl-1,3-thiazol-5-yl]- 3-aryl-prop-2-en-1-one were prepared by piperidine mediated Claisen-Schmidt condensation of thiazolyl ketone with aromatic aldehyde. These chalcones on cyclisation gave 2-amino-6-
Venkatesan,Maruthavanan
experimental part
p. 223 - 234
(2012/03/26)

Piperidine-mediated synthesis of thiazolyl chalcones and their derivatives as potent antimicrobial agents
A series of new thiazolyl chalcones, 1-[2-amino-4-methyl-1, 3-thiazol-5-yl]-3-aryl-prop-2-en-1-one were prepared by piperidine mediated Claisen-Schmidt condensation of thiazolyl ketone with substituted aromatic aldehyde. These chalcones on cyclization gav
Venkatesan,Maruthavanan
experimental part
p. 1181 - 1186
(2011/11/04)

Discovery of N-Phenyl-4-(thiazol-5-yl)pyrimidin-2-amine aurora kinase inhibitors
Through cell-based screening of our kinase-directed compound collection, we discovered that a subset of N-phenyl-4-(thiazol-5-yl)pyrimidin-2-amines were potent cytotoxic agents against cancer cell lines, suppressed mitotic histone H3 phosphorylation, and caused aberrant mitotic phenotypes. It was subsequently established that these compounds were in fact potent inhibitors of aurora A and B kinases. It was shown that potency and selectivity of aurora kinase inhibition correlated with the presence of a substituent at the aniline para-position in these compounds. The anticancer effects of lead compound 4-methyl-5-(2-(4- morpholinophenylamino)pyrimidin-4-yl)thiazol-2-amine (18; Ki values of 8.0 and 9.2 nM for aurora A and B, respectively) were shown to emanate from cell death following mitotic failure and increased polyploidy as a consequence of cellular inhibition of aurora A and B kinases. Preliminary in vivo assessment showed that compound 18 was orally bioavailable and possessed anticancer activity. Compound 18 (CYC116) is currently undergoing phase I clinical evaluation in cancer patients.
Wang, Shudong,Midgley, Carol A.,Sca?rou, Frederic,Grabarek, Joanna B.,Griffiths, Gary,Jackson, Wayne,Kontopidis, George,McClue, Steven J.,McInnes, Campbell,Meades, Christopher,Mezna, Mokdad,Plater, Andy,Stuart, Iain,Thomas, Mark P.,Wood, Gavin,Clarke, Rosemary G.,Blake, David G.,Zheleva, Daniella I.,Lane, David P.,Jackson, Robert C.,Glover, David M.,Fischer, Peter M.
scheme or table
p. 4367 - 4378
(2010/09/04)

4′-Methyl-4,5′-bithiazole-based correctors of defective ΔF508-CFTR cellular processing
The synthesis and ΔF508-CFTR corrector activity of a 148-member methylbithiazole-based library are reported. Synthetic routes were devised and optimized to generate methylbithiazole analogs in four steps. Corrector potency and efficacy were assayed using epithelial cells expressing human ΔF508-CFTR. These structure-activity data establish that the bithiazole substructure plays a critical function; eight novel methylbithiazole correctors were identified with low micromolar potencies.
Yoo, Choong Leol,Yu, Gui Jun,Yang, Baoxue,Robins, Lori I.,Verkman,Kurth, Mark J.
p. 2610 - 2614
(2008/12/21)

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)

2-Anilino-4-(thiazol-5-yl)pyrimidine CDK Inhibitors: Synthesis, SAR Analysis, X-ray Crystallography, and Biological Activity
Following the identification through virtual screening of 4-(2,4-dimethyl-thiazol-5-yl)pyrimidin-2-ylamines as moderately potent inhibitors of cyclin-dependent kinase-2 (CDK2), a CDK inhibitor analogue program was initiated. The first aims were to optimize potency and to evaluate the cellular mode of action of lead candidate molecules. Here the synthetic chemistry, the structure-guided design approach, and the structure-activity relationships (SARs) that led to the discovery of 2-anilino-4-(thiazol-5-yl)pyrimidine ATP-antagonistic CDK2 inhibitors, many with very low nM Kis against CDK2, are reported. Furthermore, X-ray crystal structures of four representative analogues from our chemical series in complex with CDK2 are presented, and these structures are used to rationalize the observed biochemical SARs. Finally results are reported that show, using the most potent CDK2 inhibitor compound from the current series, that the observed antiproliferative and proapoptotic effects are consistent with cellular CDK2 and CDK9 inhibition.
Wang, Shudong,Meades, Christopher,Wood, Gavin,Osnowski, Andrew,Anderson, Sian,Yuill, Rhoda,Thomas, Mark,Mezna, Mokdad,Jackson, Wayne,Midgley, Carol,Griffiths, Gary,Fleming, Ian,Green, Simon,McNae, Iain,Wu, Su-Ying,McInnes, Campbell,Zheleva, Daniella,Walkinshaw, Malcolm D.,Fischer, Peter M.
p. 1662 - 1675
(2007/10/03)

Selective regeneration of carbonyl compounds from aldoximes and ketoximes, catalyzed by FeCl3 and SeO2
An oxidative deblocking procedure of aldoximes using FeCl3 and ketoximes using SeO2 in aprotic solvent is reported. Reaction yields are competitive as compared to previous methods. Reactions are easy to work and conditions are mild. Some important features of FeCl3 are mentioned.
Hangarge,Mane,Chavan,Shingare
p. 1302 - 1304
(2007/10/03)

STUDIES WITH POLYFUNCTIONALLY SUBSTITUTED HETEROAROMATICS: THE REACTIVITY OF ALKYLAZOLES TOWARDS ELECTROPHILIC REAGENTS
Several new condensed thiadiazoles and thiazoles are synthesized.The reactivity of alkylazoles towards electrophilic reagents is reported.New synthesis of thienylthiadiazoles, thiadiazolopyridines and pyridazines could be achieved.Key words: Thiazoles and thiadiazoles, alkylheteroaromatics, and nucleophilic reagents and alkylazoles.
Zayed, Salem E.,Aziz, Suzan Ibrahim,Erian, Ayman Wahba,Mohareb, Rafat Milad,Elmaged, Eiman I. Abou,et al.
p. 51 - 58
(2007/10/02)

Thiazole derivatives and pharmaceutical composition comprising the same
The invention relates to novel pharmaceutical compounds for treatment for ulcer of the formula: STR1 wherein R1 is lower alkyl, carboxy, hydroxymethyl, halomethyl, lower alkylthiomethyl or hydroxyiminomethyl, R2 is hydrogen, hydroxy, lower alkyl, pyridyl, amino, lower alkylamino, pyridylamino or guanidino optionally substituted with dimethylaminomethylene, R3 is dihydroisoquinolyl which may be substituted with halogen, lower alkyl, lower alkoxy, carboxy, hydroxy, pyridyl, amino, lower alkylamino, pyridylamino or guanidino, Q is --CO--, and n is an integer of 0 or 1, and pharmaceutically acceptable salts thereof.
-
(2008/06/13)

Facile Synthesis of Aminothiazoles
The reaction of thioureas with ketones in the presence of N-bromosuccinimide furnishes 2-aminothiazoles.The method is quick, convenient and versatile.
Dahiya, Rajinder,Pujari, H. K.
p. 966
(2007/10/02)