Literature DB >> 19552465

Syntheses and biological activity studies of novel sterol analogs from nitroso Diels-Alder reactions of ergosterol.

Baiyuan Yang1, Patricia A Miller, Ute Möllmann, Marvin J Miller.   

Abstract

A series of novel sterol analogs was prepared using nitroso Diels-Alder reactions with ergosterol. Most cycloaddition reactions proceeded in an excellent regio- and stereoselective fashion. Further N-O bond cleavage of cycloadducts generated compounds with biological activity in PC-3 and MCF-7 cancer cell lines.

Entities:  

Mesh：

Substances：

Year:  2009        PMID： 19552465      PMCID： PMC2759323          DOI： 10.1021/ol900997t

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  14 in total

Review 1.  New targets and delivery systems for antifungal therapy.

Authors:  T J Walsh; M A Viviani; E Arathoon; C Chiou; M Ghannoum; A H Groll; F C Odds
Journal:  Med Mycol       Date:  2000       Impact factor: 4.076

Review 2.  Natural products as sources of new drugs over the period 1981-2002.

Authors:  David J Newman; Gordon M Cragg; Kenneth M Snader
Journal:  J Nat Prod       Date:  2003-07       Impact factor: 4.050

Review 3.  Natural products to drugs: natural product derived compounds in clinical trials.

Authors:  Mark S Butler
Journal:  Nat Prod Rep       Date:  2005-03-08       Impact factor: 13.423

4.  Stereochemistry of yeast delta 24-sterol methyl transferase.

Authors:  A P Acuna-Johnson; A C Oehlschlager; A M Pierce; H D Pierce; E K Czyzewska
Journal:  Bioorg Med Chem       Date:  1997-05       Impact factor: 3.641

5.  SOLAR ultraviolet radiation and vitamin D: a historical perspective.

Authors:  Kumaravel Rajakumar; Susan L Greenspan; Stephen B Thomas; Michael F Holick
Journal:  Am J Public Health       Date:  2007-08-29       Impact factor: 9.308

6.  Substrate-based inhibitors of the (S)-adenosyl-L-methionine:delta24(25)- to delta24(28)-sterol methyl transferase from Saccharomyces cerevisiae.

Authors:  W D Nes; D Guo; W Zhou
Journal:  Arch Biochem Biophys       Date:  1997-06-01       Impact factor: 4.013

7.  Synthesis of 25-aminosterols, new antifungal agents.

Authors:  P Beuchet; M Dherbomez; L Elkiel; G Charles; Y Letourneux
Journal:  Bioorg Med Chem Lett       Date:  1999-06-07       Impact factor: 2.823

8.  Antitumor sterols from the mycelia of Cordyceps sinensis.

Authors:  J W Bok; L Lermer; J Chilton; H G Klingeman; G H Towers
Journal:  Phytochemistry       Date:  1999-08       Impact factor: 4.072

Review 9.  Ergosterol biosynthesis inhibition: a target for antifungal agents.

Authors:  K Barrett-Bee; G Dixon
Journal:  Acta Biochim Pol       Date:  1995       Impact factor: 2.149

10.  Binding of rapamycin analogs to calcium channels and FKBP52 contributes to their neuroprotective activities.

Authors:  Benfang Ruan; Kevin Pong; Flora Jow; Mark Bowlby; Robert A Crozier; Danni Liu; Shi Liang; Yi Chen; Mary Lynn Mercado; Xidong Feng; Frann Bennett; David von Schack; Leonard McDonald; Margaret M Zaleska; Andrew Wood; Peter H Reinhart; Ronald L Magolda; Jerauld Skotnicki; Menelas N Pangalos; Frank E Koehn; Guy T Carter; Magid Abou-Gharbia; Edmund I Graziani
Journal:  Proc Natl Acad Sci U S A       Date:  2007-12-27       Impact factor: 11.205
View more
  9 in total

1.  A new sensitive LC/MS/MS analysis of vitamin D metabolites using a click derivatization reagent, 2-nitrosopyridine.

Authors:  Debin Wan; Jun Yang; Bogdan Barnych; Sung Hee Hwang; Kin Sing Stephen Lee; Yongliang Cui; Jun Niu; Mitchell A Watsky; Bruce D Hammock
Journal:  J Lipid Res       Date:  2017-02-01       Impact factor: 5.922

2.  Synthesis of unique scaffolds via Diels-Alder cycloadditions of tetrasubstituted cyclohexadienes.

Authors:  Amanda L Jones; John K Snyder
Journal:  Org Lett       Date:  2010-04-02       Impact factor: 6.005

Review 3.  Nitroso Diels-Alder (NDA) reaction as an efficient tool for the functionalization of diene-containing natural products.

Authors:  Serena Carosso; Marvin J Miller
Journal:  Org Biomol Chem       Date:  2014-10-14       Impact factor: 3.876

4.  N-O chemistry for antibiotics: discovery of N-alkyl-N-(pyridin-2-yl)hydroxylamine scaffolds as selective antibacterial agents using nitroso Diels-Alder and ene chemistry.

Authors:  Timothy A Wencewicz; Baiyuan Yang; James R Rudloff; Allen G Oliver; Marvin J Miller
Journal:  J Med Chem       Date:  2011-09-15       Impact factor: 7.446

5.  Iminonitroso ene reactions: experimental studies on reactivity, regioselectivity and enantioselectivity.

Authors:  Baiyuan Yang; Marvin J Miller
Journal:  Tetrahedron Lett       Date:  2010-01-13       Impact factor: 2.415

Review 6.  Chemo- and site-selective derivatizations of natural products enabling biological studies.

Authors:  Omar Robles; Daniel Romo
Journal:  Nat Prod Rep       Date:  2014-03       Impact factor: 13.423

7.  Preparation and biological evaluation of novel leucomycin analogs derived from nitroso Diels-Alder reactions.

Authors:  Baiyuan Yang; Tina Zöllner; Peter Gebhardt; Ute Möllmann; Marvin J Miller
Journal:  Org Biomol Chem       Date:  2009-12-11       Impact factor: 3.876

8.  Regio- and stereoselective indium triflate-mediated nucleophilic ring-opening reactions of 3-aza-2-oxabicyclo[2.2.1]hept-5-ene and -[2.2.2]oct-5-ene systems.

Authors:  Baiyuan Yang; Marvin J Miller
Journal:  J Org Chem       Date:  2009-10-16       Impact factor: 4.354

Review 9.  Stereo- and regioselectivity of the hetero-Diels-Alder reaction of nitroso derivatives with conjugated dienes.

Authors:  Lucie Brulíková; Aidan Harrison; Marvin J Miller; Jan Hlaváč
Journal:  Beilstein J Org Chem       Date:  2016-09-01       Impact factor: 2.883
  9 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.