Literature DB >> 18004798

Total synthesis and absolute configuration of laurenditerpenol: a hypoxia inducible factor-1 activation inhibitor.

Amar G Chittiboyina1, Gundluru Mahesh Kumar, Paulo B Carvalho, Yang Liu, Yu-Dong Zhou, Dale G Nagle, Mitchell A Avery.   

Abstract

The absolute stereo structure of the natural product laurenditerpenol (1S, 6R, 7S, 10R, 11R, 14S, 15R) has been accomplished from eight plausible stereoisomers by its first asymmetric total synthesis in a highly convergent and flexible synthetic pathway. Six stereoisomers of laurenditerpenol were synthesized and evaluated for their biological activity.

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Year:  2007        PMID： 18004798      PMCID： PMC2911032          DOI： 10.1021/jm7011062

Source DB:  PubMed          Journal:  J Med Chem        ISSN： 0022-2623            Impact factor:   7.446


  14 in total

Review 1.  HIF-1 as a target for drug development.

Authors:  Amato Giaccia; Bronwyn G Siim; Randall S Johnson
Journal:  Nat Rev Drug Discov       Date:  2003-10       Impact factor: 84.694

Review 2.  Hypoxia: importance in tumor biology, noninvasive measurement by imaging, and value of its measurement in the management of cancer therapy.

Authors:  James L Tatum; Gary J Kelloff; Robert J Gillies; Jeffrey M Arbeit; J Martin Brown; K S Clifford Chao; J Donald Chapman; William C Eckelman; Anthony W Fyles; Amato J Giaccia; Richard P Hill; Cameron J Koch; Murali Cherukuri Krishna; Kenneth A Krohn; Jason S Lewis; Ralph P Mason; Giovanni Melillo; Anwar R Padhani; Garth Powis; Joseph G Rajendran; Richard Reba; Simon P Robinson; Gregg L Semenza; Harold M Swartz; Peter Vaupel; David Yang; Barbara Croft; John Hoffman; Guoying Liu; Helen Stone; Daniel Sullivan
Journal:  Int J Radiat Biol       Date:  2006-10       Impact factor: 2.694

3.  HIF-1 alpha is required for solid tumor formation and embryonic vascularization.

Authors:  H E Ryan; J Lo; R S Johnson
Journal:  EMBO J       Date:  1998-06-01       Impact factor: 11.598

4.  Enantioselective total synthesis of 1-epi-pathylactone A.

Authors:  Angéline Chanu; Imad Safir; Ramkrishna Basak; Angèle Chiaroni; Siméon Arseniyadis
Journal:  Org Lett       Date:  2007-03-06       Impact factor: 6.005

5.  Hypoxia-inducible factor-1alpha is a positive factor in solid tumor growth.

Authors:  H E Ryan; M Poloni; W McNulty; D Elson; M Gassmann; J M Arbeit; R S Johnson
Journal:  Cancer Res       Date:  2000-08-01       Impact factor: 12.701

6.  Asymmetric total syntheses of (+)-cheimonophyllon e and (+)-cheimonophyllal.

Authors:  Ken-Ichi Takao; Tomohiro Tsujita; Manabu Hara; Kin-Ichi Tadano
Journal:  J Org Chem       Date:  2002-09-20       Impact factor: 4.354

7.  Convergent enantioselective synthesis of vinigrol, an architecturally novel diterpenoid with potent platelet aggregation inhibitory and antihypertensive properties. 1. Application of anionic sigmatropy to construction of the octalin substructure.

Authors:  Leo A Paquette; Ronan Guevel; Shuichi Sakamoto; In Ho Kim; Jason Crawford
Journal:  J Org Chem       Date:  2003-08-08       Impact factor: 4.354

8.  The hypoxia-inducible factor-1 alpha is a negative factor for tumor therapy.

Authors:  Annika Unruh; Anke Ressel; Hamid G Mohamed; Randall S Johnson; Roger Nadrowitz; Eckart Richter; Dörthe M Katschinski; Roland H Wenger
Journal:  Oncogene       Date:  2003-05-22       Impact factor: 9.867

Review 9.  Targeting HIF-1 for cancer therapy.

Authors:  Gregg L Semenza
Journal:  Nat Rev Cancer       Date:  2003-10       Impact factor: 60.716

Review 10.  Targeting hypoxia cell signaling for cancer therapy.

Authors:  Giovanni Melillo
Journal:  Cancer Metastasis Rev       Date:  2007-06       Impact factor: 9.264
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  6 in total

1.  Marine Natural Products as Inhibitors of Hypoxic Signaling in Tumors.

Authors:  Dale G Nagle; Yu-Dong Zhou
Journal:  Phytochem Rev       Date:  2009-06       Impact factor: 5.374

2.  Thyrsiferol Inhibits Mitochondrial Respiration and HIF-1 Activation.

Authors:  Fakhri Mahdi; Miriam Falkenberg; Efstathia Ioannou; Vassilios Roussis; Yu-Dong Zhou; Dale G Nagle
Journal:  Phytochem Lett       Date:  2011-06       Impact factor: 1.679

3.  Molecular-targeted antitumor agents. 19. Furospongolide from a marine Lendenfeldia sp. sponge inhibits hypoxia-inducible factor-1 activation in breast tumor cells.

Authors:  Yang Liu; Rui Liu; Shui-Chun Mao; J Brian Morgan; Mika B Jekabsons; Yu-Dong Zhou; Dale G Nagle
Journal:  J Nat Prod       Date:  2008-11-06       Impact factor: 4.050

Review 4.  Marine antitumor drugs: status, shortfalls and strategies.

Authors:  Ira Bhatnagar; Se-Kwon Kim
Journal:  Mar Drugs       Date:  2010-10-15       Impact factor: 5.118

5.  Dactyloditerpenol acetate, a new prenylbisabolane-type diterpene from Aplysia dactylomela with significant in vitro anti-neuroinflammatory activity.

Authors:  Carlos Jiménez-Romero; Alejandro M S Mayer; Abimael D Rodríguez
Journal:  Bioorg Med Chem Lett       Date:  2013-11-14       Impact factor: 2.823

Review 6.  Marine-derived angiogenesis inhibitors for cancer therapy.

Authors:  Ying-Qing Wang; Ze-Hong Miao
Journal:  Mar Drugs       Date:  2013-03-15       Impact factor: 5.118
  6 in total

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