- Properly tuned first fluoride-catalyzed TGME-mediated amination process for chloroimidazoles: Inexpensive technology for antihistaminic norastemizole
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Fluoride-catalyzed amination process of chloroimidazole 1 proved to be a practical and inexpensive procedure for the preparation of the antihistaminic, norastemizole.
- Senanayake, Chris H.,Hong, Yaping,Xiang, Tingjian,Scott Wilkinson,Bakale, Roger P.,Jurgens, Alex R.,Pippert, Mark F.,Butler, Hal T.,Wald, Stephen A.
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Read Online
- A short synthesis of astemizole
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The synthesis of astemizole 6, a potent H1-antihistaminic agent, was achieved in 20% overall yield. Compound 6 was obtained in high purity and on a multigram scale starting from 2-hydroxybenzimidazole.
- De Parrodi, Cecilia Anaya,Quintero-Cortes, Leticia,Sandoval-Ramirez, Jesus
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Read Online
- Synthesis and biological evaluation of 2,3-dihydroimidazo[1,2-a] benzimidazole derivatives against Leishmania donovani and Trypanosoma cruzi
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A high-throughput (HTS) and high-content screening (HCS) campaign of a commercial library identified 2,3-dihydroimidazo[1,2-a]benzimidazole analogues as a novel class of anti-parasitic agents. A series of synthetic derivatives were evaluated for their in vitro anti-leishmanial and anti-trypanosomal activities against Leishmania donovani and Trypanosoma cruzi, which have been known as the causative parasites for visceral leishmaniasis and Chagas disease, respectively. In the case of Leishmania, the compounds were tested in both intracellular amastigote and extracellular promastigote assays. Compounds 4 and 24 showed promising anti-leishmanial activity against intracellular L. donovani (3.05 and 5.29 μM, respectively) and anti-trypanosomal activity against T. cruzi (1.10 and 2.10 μM, respectively) without serious cytotoxicity toward THP-1 and U2OS cell lines.
- Oh, Sangmi,Kim, Sungbum,Kong, Sunju,Yang, Gyongseon,Lee, Nakyung,Han, Dawoon,Goo, Junghyun,Siqueira-Neto, Jair L.,Freitas-Junior, Lucio H.,Song, Rita
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p. 395 - 403
(2014/08/05)
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- Synthesis and biological evaluation of 2,3-dihydroimidazo[1,2-a] benzimidazole derivatives against Leishmania donovani and Trypanosoma cruzi
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A high-throughput (HTS) and high-content screening (HCS) campaign of a commercial library identified 2,3-dihydroimidazo[1,2-a]benzimidazole analogues as a novel class of anti-parasitic agents. A series of synthetic derivatives were evaluated for their in vitro anti-leishmanial and anti-trypanosomal activities against Leishmania donovani and Trypanosoma cruzi, which have been known as the causative parasites for visceral leishmaniasis and Chagas disease, respectively. In the case of Leishmania, the compounds were tested in both intracellular amastigote and extracellular promastigote assays. Compounds 4 and 24 showed promising anti-leishmanial activity against intracellular L. donovani (3.05 and 5.29 μM, respectively) and anti-trypanosomal activity against T. cruzi (1.10 and 2.10 mM, respectively) without serious cytotoxicity toward THP-1 and U2OS cell lines.
- Oh, Sangmi,Kim, Sungbum,Kong, Sunju,Yang, Gyongseon,Lee, Nakyung,Han, Dawoon,Goo, Junghyun,Siqueira-Neto, Jair L.,Freitas-Junior, Lucio H.,Song, Rita
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p. 395 - 403
(2015/03/13)
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- Discovery of novel, orally available benzimidazoles as melanin concentrating hormone receptor 1 (MCHR1) antagonists
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Melanin concentrating hormone (MCH) is an important mediator of energy homeostasis and plays role in several disorders such as obesity, stress, depression and anxiety. The synthesis and biological evaluation of novel benzimidazole derivatives as MCHR1 antagonists are described. The in vivo proof of principle for weight loss with a lead compound from this series is exemplified.
- Sasmal, Pradip K.,Sasmal, Sanjita,Rao, P. Tirumala,Venkatesham,Roshaiah,Abbineni, Chandrasekhar,Khanna, Ish,Jadhav, Vikram P.,Suresh,Talwar, Rashmi,Muzeeb, Syed,Receveur, Jean-Marie,Frimurer, Thomas M.,Rist, ?ystein,Elster, Lisbeth,H?gberg, Thomas
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scheme or table
p. 5443 - 5448
(2011/01/03)
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- Copper-catalyzed intramolecular cyclization to N-substituted 1,3-dihydrobenzimidazol-2-ones
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(Chemical Equation Presented) An efficient and convenient method was developed for preparing N-substituted 1,3-dihydrobenzimidazol-2-ones from Na?2-substituted N-(2-halophenyl)ureas via a CuI/DBU-catalyzed cyclization in DMSO under microwave heating. High yields were obtained and a variety of functional groups were tolerated under these conditions, including Na?2-aryl, alkyl, heterocyclic, various N-(substituted 2-halophenyl) and N-(2-iodopyridyl)ureas. ? 2008 American Chemical Society.
- Li, Zhaoguang,Sun, Hongbin,Jiang, Hualiang,Liu, Hong
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supporting information; experimental part
p. 3263 - 3266
(2009/05/11)
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- Copper-catalyzed intramolecular N-arylation of ureas in water: a novel entry to benzoimidazolones
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The copper-catalyzed intramolecular N-arylation of 2-bromoarylureas performed in water leading to the benzo[d]imidazolone framework is reported. The scope of the methodology presented herein proved to?be broad and afforded a significant number of benzoimidazolones in good to excellent yields. The reported protocol is based on the use of CuI and TMEDA acting both as the ligand and as the base in a water solution, which allows for the easy separation of the catalyst containing aqueous phase from the products by simple extraction. Additionally, the N- versus O-arylation competitive processes are also discussed.
- Barbero, Nekane,Carril, Mónica,SanMartin, Raul,Domínguez, Esther
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p. 7283 - 7288
(2008/09/21)
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- A New Approach to 1-Alkyl-1,3-dihydro-2H-benzimidazol-2-ones
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A new procedure for preparing 1-alkyl-1,3-dihydro-2H-benzimidazol-2-ones from o-nitroanilines by succesive ethoxycarbonylation, catalytic hydrogenation and thermal cyclization under neutral conditions is described. - (Keywords: Thermal cyclization)
- Gomez-Parra, Vicente,Sanchez, Felix,Torres, Tomas
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p. 639 - 644
(2007/10/02)
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