Literature DB >> 26282828

A twist of nature--the significance of atropisomers in biological systems.

Jamie E Smyth1, Nicholas M Butler1, Paul A Keller1.   

Abstract

Recently identified natural atropisomeric compounds with potential medicinal applications are presented. The ability of natural receptors to possess differential binding between atropisomers is an important factor when considering active and inactive atropisomeric drugs, and has required the development of new techniques for atropselective synthesis of desired targets. Advances in this field therefore have significant relevance to modern pharmaceutical and medicinal chemistry. The atropisomeric natural products discussed include hibarimicinone, flavomannins, talaromannins, viriditoxin, rugulotrosin A, abyssomicin C, marinopyrroles, dixiamycins, streptorubin B, ustiloxins A-F, haouamine A, bisnicalaterines, and tedarene B, all of which show significant potential as leads in antibiotic, antiviral and anticancer studies. The importance for the development of common practices regarding atropisomer recognition and classification is also emphasized.

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Year:  2015        PMID: 26282828     DOI: 10.1039/c4np00121d

Source DB:  PubMed          Journal:  Nat Prod Rep        ISSN: 0265-0568            Impact factor:   13.423


  32 in total

1.  Towards a Catalytic Atroposelective Synthesis of Diaryl Ethers via C(sp 2)-H Alkylation Using Nitroalkanes.

Authors:  Andrew N Dinh; Ryan R Noorbehesht; Sean T Toenjes; Amy C Jackson; Mirza A Saputra; Sean M Maddox; Jeffrey L Gustafson
Journal:  Synlett       Date:  2018-07-31       Impact factor: 2.454

2.  Catalytic enantioselective synthesis of atropisomeric biaryls by a cation-directed O-alkylation.

Authors:  John D Jolliffe; Roly J Armstrong; Martin D Smith
Journal:  Nat Chem       Date:  2017-01-23       Impact factor: 24.427

3.  Discovery of an Atropisomeric PI3Kβ Selective Inhibitor through Optimization of the Hinge Binding Motif.

Authors:  Stephane Perreault; Fatima Arjmand; Jayaraman Chandrasekhar; Jia Hao; Kathleen S Keegan; David Koditek; Eve-Irene Lepist; Clinton K Matson; Mary E McGrath; Leena Patel; Kassandra Sedillo; Joseph Therrien; Nicholas A Till; Adrian Tomkinson; Jennifer Treiberg; Yelena Zherebina; Gary Phillips
Journal:  ACS Med Chem Lett       Date:  2020-04-13       Impact factor: 4.345

Review 4.  Pharmacognosy in the digital era: shifting to contextualized metabolomics.

Authors:  Pierre-Marie Allard; Jonathan Bisson; Antonio Azzollini; Guido F Pauli; Geoffrey A Cordell; Jean-Luc Wolfender
Journal:  Curr Opin Biotechnol       Date:  2018-02-27       Impact factor: 9.740

5.  Asymmetric Catalysis upon Helically Chiral Loratadine Analogues Unveils Enantiomer-Dependent Antihistamine Activity.

Authors:  Elizabeth A Stone; Kara J Cutrona; Scott J Miller
Journal:  J Am Chem Soc       Date:  2020-07-09       Impact factor: 15.419

6.  Enantioselective bromination of axially chiral cyanoarenes in the presence of bifunctional organocatalysts.

Authors:  Yuuki Wada; Akira Matsumoto; Keisuke Asano; Seijiro Matsubara
Journal:  RSC Adv       Date:  2019-10-04       Impact factor: 4.036

Review 7.  Cryptic halogenation reactions in natural product biosynthesis.

Authors:  Sanjoy Adak; Bradley S Moore
Journal:  Nat Prod Rep       Date:  2021-10-20       Impact factor: 15.111

8.  Computationally Assisted Mechanistic Investigation and Development of Pd-Catalyzed Asymmetric Suzuki-Miyaura and Negishi Cross-Coupling Reactions for Tetra-ortho-Substituted Biaryl Synthesis.

Authors:  Nitinchandra Dahyabhai Patel; Joshua D Sieber; Sergei Tcyrulnikov; Bryan J Simmons; Daniel Rivalti; Krishnaja Duvvuri; Yongda Zhang; Donghong A Gao; Keith R Fandrick; Nizar Haddad; Kendricks So Lao; Hari Prasad Reddy Mangunuru; Soumik Biswas; Bo Qu; Nelu Grinberg; Scott Pennino; Heewon Lee; Jinhua J Song; B Frank Gupton; Neil K Garg; Marisa C Kozlowski; Chris H Senanayake
Journal:  ACS Catal       Date:  2018-09-20       Impact factor: 13.084

9.  Structural and Atropisomeric Factors Governing the Selectivity of Pyrimido-benzodiazipinones as Inhibitors of Kinases and Bromodomains.

Authors:  Jinhua Wang; Tatiana Erazo; Fleur M Ferguson; Dennis L Buckley; Nestor Gomez; Pau Muñoz-Guardiola; Nora Diéguez-Martínez; Xianming Deng; Mingfeng Hao; Walter Massefski; Oleg Fedorov; Nana Kwaku Offei-Addo; Paul M Park; Lingling Dai; Amy DiBona; Kelly Becht; Nam Doo Kim; Michael R McKeown; Justin M Roberts; Jinwei Zhang; Taebo Sim; Dario R Alessi; James E Bradner; Jose M Lizcano; Stephen C Blacklow; Jun Qi; Xiang Xu; Nathanael S Gray
Journal:  ACS Chem Biol       Date:  2018-08-31       Impact factor: 5.100

Review 10.  Bacterial terpenome.

Authors:  Jeffrey D Rudolf; Tyler A Alsup; Baofu Xu; Zining Li
Journal:  Nat Prod Rep       Date:  2021-05-26       Impact factor: 15.111

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