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Literature DB >> 22923851

Synthesis of Tetrazolo-Fused Benzodiazepines and Benzodiazepinones by a Two-Step Protocol Using an Ugi-Azide Reaction for Initial Diversity Generation.

Steven Gunawan¹, Muhammad Ayaz, Fabio De Moliner, Brendan Frett, Christine Kaiser, Nina Patrick, Zhigang Xu, Christopher Hulme.

Abstract

A two-step strategy for the synthesis of arrays of tricyclic tetrazolo-fused benzodiazepines and benzodiazepinones has been investigated. The protocol uses ortho-N-Boc phenylisocyanides and phenylglyoxaldehydes or ethyl glyoxylate in the 4-component Ugi-Azide reaction to afford MCR (Multi Component Reactions) derived adducts equipped with the desired diversity inputs. A subsequent acidic treatment (TFA/DCE) allows a simultaneous deprotection-cyclization leading to the final products.

Entities: Chemical Disease Gene

Year: 2012 PMID： 22923851 PMCID： PMC3423981 DOI： 10.1016/j.tet.2012.04.068

Source DB: PubMed Journal: Tetrahedron ISSN： 0040-4020 Impact factor: 2.457

23 in total

1. Benzodiazepinedione inhibitors of the Hdm2:p53 complex suppress human tumor cell proliferation in vitro and sensitize tumors to doxorubicin in vivo.

Authors: Holly K Koblish; Shuyuan Zhao; Carol F Franks; Robert R Donatelli; Rose M Tominovich; Louis V LaFrance; Kristi A Leonard; Joan M Gushue; Daniel J Parks; Raul R Calvo; Karen L Milkiewicz; Juan José Marugán; Pierre Raboisson; Maxwell D Cummings; Bruce L Grasberger; Dana L Johnson; Tianbao Lu; Christopher J Molloy; Anna C Maroney
Journal: Mol Cancer Ther Date: 2006-01 Impact factor: 6.261

2. Efficient synthesis of arrays of amino acid derived Ugi products with subsequent amidation.

Authors: Wei Wang; Alexander Dömling
Journal: J Comb Chem Date: 2009 May-Jun

3. Potent, selective, orally active 3-oxo-1,4-benzodiazepine GPIIb/IIIa integrin antagonists.

Authors: J M Samanen; F E Ali; L S Barton; W E Bondinell; J L Burgess; J F Callahan; R R Calvo; W Chen; L Chen; K Erhard; G Feuerstein; R Heys; S M Hwang; D R Jakas; R M Keenan; T W Ku; C Kwon; C P Lee; W H Miller; K A Newlander; A Nichols; M Parker; C E Peishoff; G Rhodes; S Ross; A Shu; R Simpson; D Takata; T O Yellin; I Uzsinskas; J W Venslavsky; C K Yuan; W F Huffman
Journal: J Med Chem Date: 1996-12-06 Impact factor: 7.446

4. Discovery of potent nonpeptide vitronectin receptor (alpha v beta 3) antagonists.

Authors: R M Keenan; W H Miller; C Kwon; F E Ali; J F Callahan; R R Calvo; S M Hwang; K D Kopple; C E Peishoff; J M Samanen; A S Wong; C K Yuan; W F Huffman
Journal: J Med Chem Date: 1997-07-18 Impact factor: 7.446

5. Concise route to a series of novel 3-(tetrazol-5-yl)quinoxalin-2(1H)-ones.

Authors: Steven Gunawan; Gary Nichol; Christopher Hulme
Journal: Tetrahedron Lett Date: 2012-01-28 Impact factor: 2.415

6. Two step syntheses of fused quinoxaline-benzodiazepines and bis-benzodiazepines.

Authors: Zhigang Xu; Justin Dietrich; Arthur Y Shaw; Christopher Hulme
Journal: Tetrahedron Lett Date: 2010-08-25 Impact factor: 2.415

7. Synthesis and anti-HIV-1 activity of 4,5,6,7-tetrahydro-5-methylimidazo [4,5,1-jk][1,4]benzodiazepin-2(1H)-one (TIBO) derivatives. 3.

Authors: H J Breslin; M J Kukla; D W Ludovici; R Mohrbacher; W Ho; M Miranda; J D Rodgers; T K Hitchens; G Leo; D A Gauthier
Journal: J Med Chem Date: 1995-03-03 Impact factor: 7.446

8. Applications of multicomponent reactions to the synthesis of diverse heterocyclic scaffolds.

Authors: James D Sunderhaus; Stephen F Martin
Journal: Chemistry Date: 2009 Impact factor: 5.236

9. Novel multicomponent one-pot synthesis of tetrahydro-1H-1,5-benzodiazepine-2-carboxamide derivatives.

Authors: Ahmad Shaabani; Ali Maleki; Hamid Mofakham
Journal: J Comb Chem Date: 2008-06-14

10. Synthesis of benzodiazepine beta-turn mimetics by an Ugi 4CC/Staudinger/aza-Wittig sequence. Solving the conformational behavior of the Ugi 4CC adducts.

Authors: María Sañudo; María García-Valverde; Stefano Marcaccini; Jacinto J Delgado; Josefa Rojo; Tomás Torroba
Journal: J Org Chem Date: 2009-03-06 Impact factor: 4.354

11 in total

1. One-pot synthesis of novel 1-(1H-tetrazol-5-yl)-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine derivatives via an Ugi-azide 4CR process.

Authors: Mehdi Ghandi; Saleh Salahi; Abuzar Taheri; Alireza Abbasi
Journal: Mol Divers Date: 2017-12-11 Impact factor: 2.943

2. Novel succinct routes to Quinoxalines and 2-Benzimidazolylquinoxalines via the Ugi reaction.

Authors: Muhammad Ayaz; Zhigang Xu; Christopher Hulme
Journal: Tetrahedron Lett Date: 2014-06-04 Impact factor: 2.415

Review 3. Tetrazoles via Multicomponent Reactions.

Authors: Constantinos G Neochoritis; Ting Zhao; Alexander Dömling
Journal: Chem Rev Date: 2019-02-01 Impact factor: 60.622

4. Aldol reactions in multicomponent reaction based domino pathways: a multipurpose enabling tool in heterocyclic chemistry.

Authors: Zhigang Xu; Fabio De Moliner; Alexandra P Cappelli; Christopher Hulme
Journal: Org Lett Date: 2013-05-29 Impact factor: 6.005