Literature DB >> 23961714

Facile one-pot assembly of imidazotriazolobenzodiazepines via indium(III)-catalyzed multicomponent reactions.

Huy H Nguyen1, Teresa A Palazzo, Mark J Kurth.   

Abstract

An operationally simple, one-pot multicomponent reaction has been developed for the assembly of 9H-benzo[f]imidazo[1,2-d][1,2,3]triazolo[1,5-a][1,4]diazepines adorned with three diversification points via an atom-economical transformation incorporating α-diketones, o-azidobenzaldehydes, propargylic amines, and ammonium acetate. This process involves tandem InCl3-catalyzed cyclocondensation and intramolecular azide-alkyne 1,3-dipolar cycloaddition reactions; optimization data, substrate scope, and mechanistic insights are discussed.

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Year:  2013        PMID： 23961714      PMCID： PMC3850773          DOI： 10.1021/ol402045h

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  19 in total

1.  Synthesis and biological evaluation of benzo[d]imidazole derivatives as potential anti-cancer agents.

Authors:  Hamad M Alkahtani; Abdullahi Y Abbas; Shudong Wang
Journal:  Bioorg Med Chem Lett       Date:  2011-12-23       Impact factor: 2.823

2.  Synthesis of angularly fused aromatic compounds from alkenyl enediynes by a tandem radical cyclization process.

Authors:  Snigdha Roy; Anakuthil Anoop; Kumar Biradha; Amit Basak
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-21       Impact factor: 15.336

3.  A one-pot-three-step route to triazolotriazepinoindazolones from oxazolino-2H-indazoles.

Authors:  Wayne E Conrad; Kevin X Rodriguez; Huy H Nguyen; James C Fettinger; Makhluf J Haddadin; Mark J Kurth
Journal:  Org Lett       Date:  2012-07-23       Impact factor: 6.005

4.  Tetrasubstituted imidazole inhibitors of cytokine release: probing substituents in the N-1 position.

Authors:  Stefan A Laufer; Werner Zimmermann; Kathrin J Ruff
Journal:  J Med Chem       Date:  2004-12-02       Impact factor: 7.446

5.  Bretazenil, a benzodiazepine receptor partial agonist, as an adjunct in the prophylactic treatment of OP poisoning.

Authors:  Z Tashma; L Raveh; H Liani; D Alkalay; S Givoni; J Kapon; G Cohen; M Alcalay; E Grauer
Journal:  J Appl Toxicol       Date:  2001-12       Impact factor: 3.446

6.  Rh2(II)-catalyzed nitro-group migration reactions: selective synthesis of 3-nitroindoles from β-nitro styryl azides.

Authors:  Benjamin J Stokes; Sheng Liu; Tom G Driver
Journal:  J Am Chem Soc       Date:  2011-03-14       Impact factor: 15.419

7.  Highly potent and orally active CCR5 antagonists as anti-HIV-1 agents: synthesis and biological activities of 1-benzazocine derivatives containing a sulfoxide moiety.

Authors:  Masaki Seto; Katsuji Aikawa; Naoki Miyamoto; Yoshio Aramaki; Naoyuki Kanzaki; Katsunori Takashima; Yoji Kuze; Yuji Iizawa; Masanori Baba; Mitsuru Shiraishi
Journal:  J Med Chem       Date:  2006-03-23       Impact factor: 7.446

8.  Click chemistry based rapid one-pot synthesis and evaluation for protease inhibition of new tetracyclic triazole fused benzodiazepine derivatives.

Authors:  Debendra K Mohapatra; Pradip K Maity; M Shabab; M I Khan
Journal:  Bioorg Med Chem Lett       Date:  2009-07-21       Impact factor: 2.823

9.  Inhibitors of human immunodeficiency virus type 1 (HIV-1) attachment. 12. Structure-activity relationships associated with 4-fluoro-6-azaindole derivatives leading to the identification of 1-(4-benzoylpiperazin-1-yl)-2-(4-fluoro-7-[1,2,3]triazol-1-yl-1h-pyrrolo[2,3-c]pyridin-3-yl)ethane-1,2-dione (BMS-585248).

Authors:  Alicia Regueiro-Ren; Qiufen M Xue; Jacob J Swidorski; Yi-Fei Gong; Marina Mathew; Dawn D Parker; Zheng Yang; Betsy Eggers; Celia D'Arienzo; Yongnian Sun; Jacek Malinowski; Qi Gao; Dedong Wu; David R Langley; Richard J Colonno; Caly Chien; Dennis M Grasela; Ming Zheng; Pin-Fang Lin; Nicholas A Meanwell; John F Kadow
Journal:  J Med Chem       Date:  2013-02-07       Impact factor: 7.446

10.  Synthesis of 1H-1,2,3-triazole linked β-lactam-isatin bi-functional hybrids and preliminary analysis of in vitro activity against the protozoal parasite Trichomonas vaginalis.

Authors:  Raghu Raj; Pardeep Singh; Nathan T Haberkern; Ryan M Faucher; Neal Patel; Kirkwood M Land; Vipan Kumar
Journal:  Eur J Med Chem       Date:  2013-03-16       Impact factor: 6.514
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  4 in total

Review 1.  Evolution of a strategy for preparing bioactive small molecules by sequential multicomponent assembly processes, cyclizations, and diversification.

Authors:  James J Sahn; Brett A Granger; Stephen F Martin
Journal:  Org Biomol Chem       Date:  2014-08-19       Impact factor: 3.876

2.  Expedient one-pot synthesis of indolo[3,2-c]isoquinolines via a base-promoted N-alkylation/tandem cyclization.

Authors:  Huy H Nguyen; James C Fettinger; Makhluf J Haddadin; Mark J Kurth
Journal:  Tetrahedron Lett       Date:  2015-09-30       Impact factor: 2.415

3.  Sequential Ugi reaction/base-induced ring closing/IAAC protocol toward triazolobenzodiazepine-fused diketopiperazines and hydantoins.

Authors:  Robby Vroemans; Fante Bamba; Jonas Winters; Joice Thomas; Jeroen Jacobs; Luc Van Meervelt; Jubi John; Wim Dehaen
Journal:  Beilstein J Org Chem       Date:  2018-03-14       Impact factor: 2.883

Review 4.  Allosteric GABAA Receptor Modulators-A Review on the Most Recent Heterocyclic Chemotypes and Their Synthetic Accessibility.

Authors:  Blanca Angelica Vega Alanis; Maria Teresa Iorio; Luca L Silva; Konstantina Bampali; Margot Ernst; Michael Schnürch; Marko D Mihovilovic
Journal:  Molecules       Date:  2020-02-24       Impact factor: 4.927
  4 in total

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