Literature DB >> 25698845

A facile synthesis of bispyrroloquinone and bispyrroloiminoquinone ring system of marine alkaloids.

Srinivasan Murugesan1, Dwayaja H Nadkarni1, Sadanandan E Velu1.   

Abstract

Bispyrroloquinone and bispyrroloiminoquinone are two important polycyclic ring systems present in biologically active marine alkaloids such as Zyzzyanones, tsitsikammamines and wakayin. A facile synthesis of these two ring systems starting from a 6-benzylamino indole-4,7-quinone or 6-benzylamino pyrroloiminoquinone is described here. This chemistry involves the construction of a pyrrole ring in a single step by treatment of the starting reagents with ethyl acetoacetate or phenylbutane-1,3-dione in the presence of ceric ammonium nitrate in MeOH/CH2Cl2 solvent.

Entities:  

Year:  2009        PMID： 25698845      PMCID： PMC4331033          DOI： 10.1016/j.tetlet.2009.04.021

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  23 in total

1.  Makaluvamines H-M and damirone C from the pohnpeian sponge Zyzzya fuliginosa.

Authors:  E W Schmidt; M K Harper; D J Faulkner
Journal:  J Nat Prod       Date:  1995-12       Impact factor: 4.050

Review 2.  Marine natural products as anticancer drugs.

Authors:  T Luke Simmons; Eric Andrianasolo; Kerry McPhail; Patricia Flatt; William H Gerwick
Journal:  Mol Cancer Ther       Date:  2005-02       Impact factor: 6.261

3.  Synthesis and in vitro evaluation of imidazole-based wakayin analogues.

Authors:  Hung Hoang; Xiaofen Huang; Edward B Skibo
Journal:  Org Biomol Chem       Date:  2008-07-16       Impact factor: 3.876

4.  Makaluvamine N: a new pyrroloiminoquinone from Zyzzya fuliginosa.

Authors:  D A Venables; G P Concepción; S S Matsumoto; L R Barrows; C M Ireland
Journal:  J Nat Prod       Date:  1997-04       Impact factor: 4.050

5.  Zyzzyanones B-D, dipyrroloquinones from the marine sponge Zyzzya fuliginosa.

Authors:  Natalia K Utkina; Aleksandra E Makarchenko; Vladimir A Denisenko
Journal:  J Nat Prod       Date:  2005-09       Impact factor: 4.050

6.  Makaluvamine P, a new cytotoxic pyrroloiminoquinone from Zyzzya cf. fuliginosa.

Authors:  A Casapullo; A Cutignano; I Bruno; G Bifulco; C Debitus; L Gomez-Paloma; R Riccio
Journal:  J Nat Prod       Date:  2001-10       Impact factor: 4.050

7.  New antiinfective and human 5-HT2 receptor binding natural and semisynthetic compounds from the Jamaican sponge Smenospongia aurea.

Authors:  Jin-Feng Hu; John A Schetz; Michelle Kelly; Jiang-Nan Peng; Kenny K H Ang; Horst Flotow; Chung Yan Leong; Siew Bee Ng; Antony D Buss; Scott P Wilkins; Mark T Hamann
Journal:  J Nat Prod       Date:  2002-04       Impact factor: 4.050

Review 8.  Pyrroloiminoquinone and related metabolites from marine sponges.

Authors:  Edith M Antunes; Brent R Copp; Michael T Davies-Coleman; Toufiek Samaai
Journal:  Nat Prod Rep       Date:  2005-01-04       Impact factor: 13.423

9.  Cytotoxic pyrroloiminoquinones from four new species of South African latrunculid sponges.

Authors:  Edith M Antunes; Denzil R Beukes; Michelle Kelly; Toufiek Samaai; Louis R Barrows; Kathryn M Marshall; Catherine Sincich; Michael T Davies-Coleman
Journal:  J Nat Prod       Date:  2004-08       Impact factor: 4.050

Review 10.  Pyrroloquinoline and pyridoacridine alkaloids from marine sources.

Authors:  Q Ding; K Chichak; J W Lown
Journal:  Curr Med Chem       Date:  1999-01       Impact factor: 4.530
View more
  3 in total

1.  Total Synthesis of Calothrixins A and B via Oxidative Radical Reaction of Cyclohexenone with Aminophenanthridinedione.

Authors:  Su Xu; Thao Nguyen; Irene Pomilio; Maria C Vitale; Sadanandan E Velu
Journal:  Tetrahedron       Date:  2014-09-02       Impact factor: 2.457

2.  Total synthesis of zyzzyanones A-D.

Authors:  Dwayaja H Nadkarni; Srinivasan Murugesan; Sadanandan E Velu
Journal:  Tetrahedron       Date:  2013-05-20       Impact factor: 2.457

3.  Synthesis of Pyrroloquinones via a CAN Mediated Oxidative Free Radical Reaction of 1,3-Dicarbonyl Compounds with Aminoquinones.

Authors:  Thao Nguyen; Dwayaja Nadkarni; Shilpa Dutta; Su Xu; Sanghun Kim; Srinivasan Murugesan; Sadanandan Velu
Journal:  J Chem       Date:  2013
  3 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.