- Copper-Promoted Cycloaddition of α-Methylenyl Isocyanides with Benzothiazoles: Tunable Access to Benzo[d]imidazothiazoles
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A tunable route to both isomers of benzo[d]imidazothiazole has been developed through copper-promoted cycloaddition of α-methylenyl isocyanides with benzothiazoles. When the C2 position of benzothiazole is linked to a C-H or C-C bond, benzo[d]imidazo[2,1-
- Wang, Jian,Li, Jing,Zhu, Qiang
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Read Online
- A new fluorescent probe based on imidazole[2,1-b]benzothiazole for sensitive and selective detection of Cu2+
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A simple fluorescent chemosensor WS1 (N'-[(Z)-1H-indazol-3-ylmethylidene]imidazo [2,1-b] [1,3]benzothiazole-2-carbohydrazide) based on imidazole [2,1-b]benzothiazole was designed and synthesized. The probe showed specific recognition towards Cu2+ through colorimetric and “turn-off” fluorescence response in MeOH/H2O (9:1 V/V) buffer solution (10 mM Tris, pH = 7.4) with detection limit of 4.32 × 10?8 M. In addition, WS1 was a reversible fluorescence probe for the detection of Cu2+, the fluorescence intensity recovered to the similar state of free WS1 as PPi was added. And it showed a favorable potency for actual water monitoring. The proposed binding mode of WS1 with Cu2+ was verified by DFT calculation using Gaussian 09.
- Wang, Hanyu,Zhao, Songfang,Xu, Yuankang,Li, Linlin,Li, Bing,Pei, Meishan,Zhang, Guangyou
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Read Online
- On water catalyst-free synthesis of benzo[: D] imidazo[2,1- b] thiazoles and novel N -alkylated 2-aminobenzo [d] oxazoles under microwave irradiation
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A highly efficient unprecedented catalyst-free microwave-assisted procedure for synthesizing benzo[d]imidazo[2,1-b]thiazoles and N-alkylated 2-aminobenzo[d]oxazol in green media was developed. The transformation provided rapid access to functionalized ben
- Mukku, Narasimharao,Maiti, Barnali
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p. 770 - 778
(2020/01/23)
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- Design and synthesis of 1,2,3-triazolo linked benzo[d]imidazo[2,1-b]thiazole conjugates as tubulin polymerization inhibitors
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1,2,3-Triazolo linked benzo[d]imidazo[2,1-b]thiazole conjugates (5a–v) were designed, synthesized and evaluated for their cytotoxic potency against some human cancer cell lines like DU-145 (prostate), HeLa (cervical), MCF-7 (breast) HepG2 (liver) and A549 (lung). Preliminary results revealed that some of these conjugates like 5f and 5k exhibited significant antiproliferative effect against human breast cancer cells (MCF-7) with IC50 values of 0.60 and 0.78?μM respectively. Flow cytometric analysis of the cell cycle demonstrated an increase in the percentage of cells in the G2/M phase which was further authenticated by elevation of cyclin B1 protein levels. Immunocytochemistry revealed loss of intact microtubule structure in cells treated with 5f and 5k, and western blot analysis revealed that these conjugates accumulated more tubulin in the soluble fraction. Moreover, the conjugates caused apoptosis of the cells that was confirmed by mitochondrial membrane potential and Annexin V-FITC assay. Molecular docking studies indicated that these conjugates occupy the colchicine binding site of the tubulin protein.
- Shaik, Siddiq Pasha,Vishnuvardhan,Sultana, Faria,Subba Rao,Bagul, Chandrakant,Bhattacharjee, Debanjan,Kapure, Jeevak Sopanrao,Jain, Nishant,Kamal, Ahmed
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p. 3285 - 3297
(2017/05/29)
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- Imidazole [2, 1-b] thiazole derivative as well as preparation method and application thereof
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The invention belongs to the field of chemical pharmaceuticals, and particularly relates to an imidazole [2, 1-b] thiazole derivative as well as a preparation method and an application thereof. The structure of the imidazole [2, 1-b] thiazole derivative i
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Paragraph 0232; 0233
(2017/01/02)
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- Discovery of imidazo[2,1- b ]thiazole HCV NS4B inhibitors exhibiting synergistic effect with other direct-acting antiviral agents
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The design, synthesis, and SAR studies of novel inhibitors of HCV NS4B based on the imidazo[2,1-b]thiazole scaffold were described. Optimization of potency with respect to genotype 1b resulted in the discovery of two potent leads 26f (EC50 = 16
- Wang, Ning-Yu,Xu, Ying,Zuo, Wei-Qiong,Xiao, Kun-Jie,Liu, Li,Zeng, Xiu-Xiu,You, Xin-Yu,Zhang, Li-Dan,Gao, Chao,Liu, Zhi-Hao,Ye, Ting-Hong,Xia, Yong,Xiong, Ying,Song, Xue-Jiao,Lei, Qian,Peng, Cui-Ting,Tang, Hong,Yang, Sheng-Yong,Wei, Yu-Quan,Yu, Luo-Ting
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p. 2764 - 2778
(2015/04/14)
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- Arylcarboxyamino-substituted diaryl ureas as potent and selective FLT3 inhibitors
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A series of diaryl ureas with an amide substitution at the 4-position was prepared and found to be potent and selective FLT3 inhibitors with good oral bioavailability and efficacy in a tumor xenograft model.
- Patel, Hitesh K.,Grotzfeld, Robert M.,Lai, Andiliy G.,Mehta, Shamal A.,Milanov, Zdravko V.,Chao, Qi,Sprankle, Kelly G.,Carter, Todd A.,Velasco, Anne Marie,Fabian, Miles A.,James, Joyce,Treiber, Daniel K.,Lockhart, David J.,Zarrinkar, Patrick P.,Bhagwat, Shripad S.
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scheme or table
p. 5182 - 5185
(2010/03/31)
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- Discovery of novel Tricyclic full agonists for the G-protein-coupled niacin receptor 109A with minimized flushing in rats
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Tricyclic analogues were rationally designed as the high affinity niacin receptor G-protein-coupled receptor 109A (GPR109A) agonists by overlapping three lead structures. Various tricyclic anthranilide and cycloalkene carboxylic acid full agonists were di
- Shen, Hong C.,Ding,Deng, Qiaolin,Wilsie, Larissa C.,Krsmanovic, Mihajlo L.,Taggart, Andrew K.,Carballo-Jane, Ester,Ren, Ning,Cai,Wu,Wu, Kenneth K.,Cheng, Kang,Chen, Qing,Wolff, Michael S.,Tong, Xinchun,Holt, Tom G.,Waters, M. Gerard,Hammond, Milton L.,Tata, James R.,Colletti, Steven L.
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supporting information; experimental part
p. 2587 - 2602
(2010/01/15)
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- Tricyclic 6-alkylidene-penems as class-D beta-lactamases inhibitors
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This invention relates to certain tricyclic 6-alkylidene penems which act as a inhibitor of class-D enzymes. β-Lactamases hydrolyze β-lactam antibiotics, and as such serve as the primary cause of bacterial resistance. The compounds of the present inventio
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Page/Page column 9
(2010/11/25)
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- Structure-activity relationship of 6-methylidene penems bearing tricyclic heterocycles as broad-spectrum β-lactamase inhibitors: Crystallographic structures show unexpected binding of 1,4-thiazepine intermediates
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The design and synthesis of a series of seven tricyclic 6-methylidene penems as novel class A and C serine β-lactamase inhibitors is described. These compounds proved to be very potent inhibitors of the TEM-1 and AmpC β-lactamases and less so against the class B metallo-β-lactamase CcrA. In combination with piperacillin, their in vitro activities enhanced susceptibility of all class C resistant strains from various bacteria. Crystallographic structures of a serine-bound reaction intermediate of 17 with the class A SHV-1 and class C GC1 enzymes have been established to resolutions of 2.0 and 1.4 A?, respectively, and refined to R-factors equal 0.163 and 0.145. In both β-lactamases, a seven-membered 1,4-thiazepine ring has formed. The stereogenic C7 atom in the ring has the R configuration in the SHV-1 intermediate and has both R and S configurations in the GC1 intermediate. Hydrophobic stacking interactions between the tricyclic C7 substituent and a tyrosine side chain, rather than electrostatic or hydrogen bonding by the C3 carboxylic acid group, dominate in both complexes. The formation of the 1,4- thiazepine ring structures is proposed based on a 7-endo-trig cyclization.
- Venkatesan, Aranapakam M.,Gu, Yansong,Santos, Osvaldo Dos,Abe, Takao,Agarwal, Atul,Yang, Youjun,Petersen, Peter J.,Weiss, William J.,Mansour, Tarek S.,Nukaga, Michiyoshi,Hujer, Andrea M.,Bonomo, Robert A.,Knox, James R.
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p. 6556 - 6568
(2007/10/03)
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- Process for preparing 6-alkylidene penem derivatives
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The present invention provides a process of making compounds of formula I, which are useful for the treatment of bacterial infection or disease.
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- HETEROTRICYCLYL 6-ALKYLIDENE-PENEMS AS ΒΕΤΑ-LACTAMASE INHIBITORS
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The present invention provides a compound of formula I, pharmaceutical compositions and the use thereof for the treatment of bacterial infection or disease in a patient in need thereof.
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Page/Page column 95-96
(2008/06/13)
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- PROCESS FOR PREPARING 6-ALKYLIDENE PENEM DERIVATIVES
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The present invention provides a process of making compounds of Formula (I), which are useful for the treatment of bacterial infection or disease.
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Page/Page column 82
(2010/02/07)
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- Synthesis, in vitro and in vivo cytotoxicity, and prediction of the intestinal absorption of substituted 2-ethoxycarbonyl-imidazo[2,1-b]benzothiazoles
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The imidazobenzothiazole compounds 3-17 together with the imidazobenzoxazole 18, and the imidazobenzoimidazole 19 were prepared and their cytotoxic activity evaluated at the National Cancer Institute (NCI) for testing against a panel of approximately 60 tumor cell lines. Compounds 5, 7, 8, and 16 exhibited interesting in vitro cytotoxic activity. The most active imidazobenzothiazole derivative 8 was further evaluated as a cytotoxic agent in the hollow fiber assay and showed a score greater than the minimum values for xenograft testing together with a net cell kill. Comparison with the results displayed in the in vivo assay by standard antitumor drugs in clinical use revealed a significant in vivo activity of the benzothiazole compound. COMPARE analyses for compounds 4-19 against the NCI's standard agent database show poor or no correlation, and it might suggest for these compounds a mechanism of action unrelated to that of any known drug. Furthermore, the benzothiazole 8 did not show significant antitumor activity in a panel of two xenotransplanted tumors (i.e. colon and non-small cell lung tumors). By computing the polar surface area of compounds 3-19 with the MAREA computer program it was established that the most active compounds 5, 7, 8, and 16 should experience good intestinal permeability. Copyright
- Trapani, Giuseppe,Franco, Massimo,Latrofa, Andrea,Reho, Antonia,Liso, Gaetano
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p. 209 - 216
(2007/10/03)
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- Synthesis and SAR study of imidazo[2,1-b]benzothiazole acids and some related compounds with anti-inflammatory and analgesic activities
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Some (un)substituted imidazo[2,1-b]benzothiazole carboxylic or acetic acids and some related compounds, i.e. imidazo[2,1-b]naphtho[2,1-d]thiazole, 4H-imidazo[2,1-c][1,4]benzothiazine, 4,5-dihydroimidazo[2,1-d][1,5]benzothiazepine carboxylic and acetic aci
- Palagiano,Arenare,De Caprariis,Grandolini,Ambrogi,Perioli,Filippelli,Falcone,Rossi
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p. 483 - 491
(2007/10/03)
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- (Imidazopyrimidin-2-yl)phenylmethanones and Related Compounds as Potential Nonsedative Anxiolytics
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Several series of heterocyclic carboxylic esters were found to be active in the benzodiazepine receptor binding assay, a typical example being ethyl 7-ethyl-5-methoxyimidazoquinoline-2-carboxylate (4b) with an IC50 of 150 nM.The correspo
- Clements-Jewery, Stephen,Danswan, Geoffrey,Gardner, Colin R.,Matharu, Saroop S.,Murdoch, Robert,et al.
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p. 1220 - 1226
(2007/10/02)
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- Synthesis and oral antiallergic activity of carboxylic acids derived from imidazo[2,1-c][1,4]benzoxazines, imidazo[1,2-a]quinolines, imidazo[1,2-a]quinoxalines, imidazo[1,2-a]quinoxalinones, pyrrolo[1,2-a]quinoxalinones, pyrrolo[2,3-a]quinoxalinones, and
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4H-Imidazo[2,1-c][1,4]benzoxazine-1-carboxylic acid (3) was found to possess potent activity in the IgE-induced rat passive cutaneous anaphylaxis model which may be predictive of clinical antiallergic activity. Compared to disodium cromoglycate (DSCG,1),
- Ager,Barnes,Danswan,Hairsine,Kay,Kennewell,Matharu,Miller,Robson,Rowlands,Tully,Westwood
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p. 1098 - 1115
(2007/10/02)
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