Literature DB >> 28631155

A simple and facile synthesis of tricyclic-fused pyrimido[4,5-b]indol-2-amines.

Wentao Gao1, Dongfang Wang1, Yang Li2.   

Abstract

In the present investigation, a simple and facile synthetic strategy for the construction of a series of structurally interesting tricyclic-fused N-alkyl-9H-pyrimido[4,5-b]indol-2-amines has been successfully achieved. Our synthesis, based on the annulation reaction between readily available 2-chloroindole-3-carbaldehydes or 3-acetyl-2-chloroindoles and guanidine nitrate using KOH as the base in refluxing EtOH medium, has the attractive features such as mild and economical reaction conditions and easy handing with lesser impact on the environment.

Entities:  

Keywords:  2-Aminopyrimidine, Pyrimido[4, 5-b]indole; Annulation reaction; Guanidine nitrate; Indole-3-carbaldehyde

Mesh:

Substances:

Year:  2017        PMID: 28631155     DOI: 10.1007/s11030-017-9757-4

Source DB:  PubMed          Journal:  Mol Divers        ISSN: 1381-1991            Impact factor:   2.943


  21 in total

1.  Fused tricyclic indoles as S1P₁ agonists with robust efficacy in animal models of autoimmune disease.

Authors:  Daniel J Buzard; Sangdon Han; Luis Lopez; Andrew Kawasaki; Jeanne Moody; Lars Thoresen; Brett Ullman; Juerg Lehmann; Imelda Calderon; Xiuwen Zhu; Tawfik Gharbaoui; Dipanjan Sengupta; Ashwin Krishnan; Yinghong Gao; Jeff Edwards; Jeremy Barden; Michael Morgan; Khawja Usmani; Chuan Chen; Abu Sadeque; Jayant Thatte; Michelle Solomon; Lixia Fu; Kevin Whelan; Ling Liu; Hussien Al-Shamma; Joel Gatlin; Minh Le; Charles Xing; Sheryll Espinola; Robert M Jones
Journal:  Bioorg Med Chem Lett       Date:  2012-05-07       Impact factor: 2.823

2.  Tyrosine kinase inhibitors. 16. 6,5,6-tricyclic benzothieno[3, 2-d]pyrimidines and pyrimido[5,4-b-] and -[4,5-b]ĭndoles as potent inhibitors of the epidermal growth factor receptor tyrosine kinase.

Authors:  H D Showalter; A J Bridges; H Zhou; A D Sercel; A McMichael; D W Fry
Journal:  J Med Chem       Date:  1999-12-30       Impact factor: 7.446

Review 3.  Variolins and related alkaloids.

Authors:  Scott R Walker; Erin J Carter; Belinda C Huff; Jonathan C Morris
Journal:  Chem Rev       Date:  2009-07       Impact factor: 60.622

4.  In-vitro antiproliferative activities and kinase inhibitory potencies of meridianin derivatives.

Authors:  Emilie Rossignol; Eric Debiton; Doriano Fabbro; Pascale Moreau; Michelle Prudhomme; Fabrice Anizon
Journal:  Anticancer Drugs       Date:  2008-09       Impact factor: 2.248

5.  Design and synthesis of new tricyclic indoles as potent modulators of the S1P1 receptor.

Authors:  Daniel J Buzard; Thomas O Schrader; Xiuwen Zhu; Juerg Lehmann; Ben Johnson; Michelle Kasem; Sun Hee Kim; Andrew Kawasaki; Luis Lopez; Jeanne Moody; Sangdon Han; Yinghong Gao; Jeff Edwards; Jeremy Barden; Jayant Thatte; Joel Gatlin; Robert M Jones
Journal:  Bioorg Med Chem Lett       Date:  2014-12-09       Impact factor: 2.823

6.  Discovery of 1-amino-5H-pyrido[4,3-b]indol-4-carboxamide inhibitors of Janus kinase 2 (JAK2) for the treatment of myeloproliferative disorders.

Authors:  Jongwon Lim; Brandon Taoka; Ryan D Otte; Kerrie Spencer; Christopher J Dinsmore; Michael D Altman; Grace Chan; Craig Rosenstein; Sujata Sharma; Hua-Poo Su; Alexander A Szewczak; Lin Xu; Hong Yin; Joan Zugay-Murphy; C Gary Marshall; Jonathan R Young
Journal:  J Med Chem       Date:  2011-09-26       Impact factor: 7.446

7.  CNS and antimalarial activity of synthetic meridianin and psammopemmin analogs.

Authors:  Matthew D Lebar; Kristopher N Hahn; Tina Mutka; Patrick Maignan; James B McClintock; Charles D Amsler; Alberto van Olphen; Dennis E Kyle; Bill J Baker
Journal:  Bioorg Med Chem       Date:  2011-08-22       Impact factor: 3.641

8.  One-pot synthesis of benzo[c]carbazoles by photochemical annulation of 2-chloroindole-3-carbaldehydes.

Authors:  Cailin Wang; Wei Zhang; Shenci Lu; Jingfei Wu; Zongjun Shi
Journal:  Chem Commun (Camb)       Date:  2008-09-12       Impact factor: 6.222

9.  Development of indole/indazole-aminopyrimidines as inhibitors of c-Jun N-terminal kinase (JNK): optimization for JNK potency and physicochemical properties.

Authors:  Leyi Gong; Xiaochun Han; Tania Silva; Yun-Chou Tan; Bindu Goyal; Parch Tivitmahaisoon; Alejandra Trejo; Wylie Palmer; Heather Hogg; Alam Jahagir; Muzaffar Alam; Paul Wagner; Karin Stein; Lubov Filonova; Brad Loe; Ferenc Makra; David Rotstein; Lubica Rapatova; James Dunn; Fengrong Zuo; Joseph Dal Porto; Brian Wong; Sue Jin; Alice Chang; Patricia Tran; Gary Hsieh; Linghao Niu; Ada Shao; Deborah Reuter; Johaness Hermann; Andreas Kuglstatter; David Goldstein
Journal:  Bioorg Med Chem Lett       Date:  2013-04-21       Impact factor: 2.823

10.  An efficient access to the synthesis of novel 12-phenylbenzo[6,7]oxepino[3,4-b]quinolin-13(6H)-one derivatives.

Authors:  Wentao Gao; Guihai Lin; Yang Li; Xiyue Tao; Rui Liu; Lianjie Sun
Journal:  Beilstein J Org Chem       Date:  2012-10-30       Impact factor: 2.883

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  1 in total

Review 1.  The Molecular Diversity of 1H-Indole-3-Carbaldehyde Derivatives and Their Role in Multicomponent Reactions.

Authors:  Ghodsi Mohammadi Ziarani; Samira Hasani; Fatemeh Mohajer; Rajender S Varma; Fatemeh Rafiee
Journal:  Top Curr Chem (Cham)       Date:  2022-04-25
  1 in total

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