Literature DB >> 29909566

One-pot synthesis of biologically active 1,2,3-trisubstituted pyrrolo[2,3-b]quinoxalines through a palladium-catalyzed reaction with internal alkyne moieties.

Ali Keivanloo1, Tayebeh Besharati-Seidani2, Babak Kaboudin3, Akihiro Yoshida4, Tsutomu Yokomatsu4.   

Abstract

Synthesis of 2,3-disubstituted 1-alkylpyrrolo[2,3-b]quinoxalines was accomplished through the reaction of 3-chloroquinoxalin-2-amines with internal alkynes in the presence of Pd(OAc)[Formula: see text], NaOAc, and KOtBu in DMSO. This method afforded desired pyrrolo[2,3-b]quinoxalines in 65-92% reaction yields. The minimum inhibition concentration and minimum bactericidal concentration determinations against Micrococcus luteus and Pseudomonas aeruginosa revealed that some of the synthesized compounds showed the same values compared to tetracycline. These compounds could be used in the future research for the development of new antibiotics.

Entities:  

Keywords:  3-b]quinoxaline; Anti-bacterial activities; Antibiotics; Internal alkyne; Palladium-catalyzed reaction; Pyrrolo[2

Mesh:

Substances:

Year:  2018        PMID: 29909566     DOI: 10.1007/s11030-018-9838-z

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


  11 in total

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Authors:  M Vaara
Journal:  Microbiol Rev       Date:  1992-09

2.  Defective expression of SIRT1 contributes to sustain inflammatory pathways in the gut.

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Journal:  Mucosal Immunol       Date:  2014-05-21       Impact factor: 7.313

Review 3.  Three stories on Eph kinase inhibitors: From in silico discovery to in vivo validation.

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4.  Discovery of novel scaffolds for Rho kinase 2 inhibitor through TRFRET-based high throughput screening assay.

Authors:  Kwang-Seok Oh; Jihye Mun; Jae Eun Cho; Sunghou Lee; Kyu Yang Yi; Chae Jo Lim; Jin Soo Lee; Whui Jung Park; Byung Ho Lee
Journal:  Comb Chem High Throughput Screen       Date:  2013-01       Impact factor: 1.339

5.  Synthesis of Novel 3-Substituted Pyrrolo[2,3-b]quinoxalines via an Intramolecular Heck Reaction on an Aminoquinoxaline Scaffold.

Authors:  Jie Jack Li
Journal:  J Org Chem       Date:  1999-10-29       Impact factor: 4.354

6.  Pyrrolo[2,3-b]quinoxalines as inhibitors of firefly luciferase: their Cu-mediated synthesis and evaluation as false positives in a reporter gene assay.

Authors:  Ali Nakhi; Md Shafiqur Rahman; Ravada Kishore; Chandana Lakshmi T Meda; Girdhar Singh Deora; Kishore V L Parsa; Manojit Pal
Journal:  Bioorg Med Chem Lett       Date:  2012-08-22       Impact factor: 2.823

7.  Ligand/PTC-free intramolecular Heck reaction: synthesis of pyrroloquinoxalines and their evaluation against PDE4/luciferase/oral cancer cell growth in vitro and zebrafish in vivo.

Authors:  P Vijaya Babu; Soumita Mukherjee; Girdhar Singh Deora; Keerthana Sarma Chennubhotla; Raghavender Medisetti; Swapna Yellanki; Pushkar Kulkarni; Shivashankar Sripelly; Kishore V L Parsa; Kiranam Chatti; K Mukkanti; Manojit Pal
Journal:  Org Biomol Chem       Date:  2013-08-29       Impact factor: 3.876

8.  Synthesis and anti-inflammatory/antioxidant activities of some new ring substituted 3-phenyl-1-(1,4-di-N-oxide quinoxalin-2-yl)-2-propen-1-one derivatives and of their 4,5-dihydro-(1H)-pyrazole analogues.

Authors:  Asunción Burguete; Eleni Pontiki; Dimitra Hadjipavlou-Litina; Raquel Villar; Esther Vicente; Beatriz Solano; Saioa Ancizu; Silvia Pérez-Silanes; Ignacio Aldana; Antonio Monge
Journal:  Bioorg Med Chem Lett       Date:  2007-10-05       Impact factor: 2.823

9.  Synthesis and application of novel sulpha drugs based on quinoxaline-2-one and/or quinoxaline-2-thione.

Authors:  I M Awad
Journal:  J Chem Technol Biotechnol       Date:  1992       Impact factor: 3.174

10.  Pyrrolo[3,2-b]quinoxaline derivatives as types I1/2 and II Eph tyrosine kinase inhibitors: structure-based design, synthesis, and in vivo validation.

Authors:  Andrea Unzue; Jing Dong; Karine Lafleur; Hongtao Zhao; Emilie Frugier; Amedeo Caflisch; Cristina Nevado
Journal:  J Med Chem       Date:  2014-07-30       Impact factor: 7.446

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  1 in total

1.  One-pot sequential coupling reactions as a new practical protocol for the synthesis of unsymmetrical 2,3-diethynyl quinoxalines and 4-ethynyl-substituted pyrrolo[1,2-a]quinoxalines.

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Journal:  Mol Divers       Date:  2020-04-16       Impact factor: 2.943

  1 in total

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