Literature DB >> 19896844

Synthesis and anticancer activity of sclerophytin-inspired hydroisobenzofurans.

T David Bateman1, Aarti L Joshi, Kwangyul Moon, Elena N Galitovskaya, Meenakshi Upreti, Timothy C Chambers, Matthias C McIntosh.   

Abstract

Three structurally related sets of hydroisobenzofuran analogs of sclerophytin A were prepared in three or four steps from (S)-(+)-carvone via an aldol-cycloaldol sequence. The most potent members of each set of analogs exhibited IC(50)'s of 1-3 microM in growth inhibitory assays against KB3 cells. The NCI 60-cell line 5-dose assay for analog 6h revealed a GI(50)=0.148 microM and LC(50)=9.36 microM for the RPMI-8226 leukemia cell line, and a GI(50)=0.552 microM and LC(50)=26.8 microM for the HOP-92 non-small cell lung cancer cell line.

Entities:  

Mesh:

Substances:

Year:  2009        PMID: 19896844      PMCID: PMC3276365          DOI: 10.1016/j.bmcl.2009.10.079

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN: 0960-894X            Impact factor:   2.823


  16 in total

1.  Structural and stereochemical reassessment of sclerophytin-type diterpenes.

Authors:  Dirk Friedrich; Leo A Paquette
Journal:  J Nat Prod       Date:  2002-02       Impact factor: 4.050

2.  Simplexins A-I, eunicellin-based diterpenoids from the soft coral Klyxum simplex.

Authors:  Shwu-Li Wu; Jui-Hsin Su; Zhi-Hong Wen; Chi-Hsin Hsu; Bo-Wei Chen; Chang-Feng Dai; Yao-Haur Kuo; Jyh-Horng Sheu
Journal:  J Nat Prod       Date:  2009-06       Impact factor: 4.050

Review 3.  Strategies for the total synthesis of C2-C11 cyclized cembranoids.

Authors:  J Michael Ellis; Michael T Crimmins
Journal:  Chem Rev       Date:  2008-12       Impact factor: 60.622

4.  Feasibility of drug screening with panels of human tumor cell lines using a microculture tetrazolium assay.

Authors:  M C Alley; D A Scudiero; A Monks; M L Hursey; M J Czerwinski; D L Fine; B J Abbott; J G Mayo; R H Shoemaker; M R Boyd
Journal:  Cancer Res       Date:  1988-02-01       Impact factor: 12.701

5.  Bioactive compounds from the gorgonian Briareum polyanthes. Correction of the structures of four asbestinane-type diterpenes.

Authors:  Claudia A Ospina; Abimael D Rodríguez
Journal:  J Nat Prod       Date:  2006-12       Impact factor: 4.050

6.  Studies directed toward the synthesis of the massileunicellins. 2.

Authors:  Yonghai Chai; Zonghong Mou; Matthias C McIntosh
Journal:  Tetrahedron Lett       Date:  2010-05-05       Impact factor: 2.415

7.  Eunicellin diterpenes from two Kenyan soft corals.

Authors:  Liat Chill; Nelly Berrer; Yehuda Benayahu; Yoel Kashman
Journal:  J Nat Prod       Date:  2005-01       Impact factor: 4.050

8.  Eunicellin-based diterpenoids, australins A-D, isolated from the soft coral Cladiella australis.

Authors:  Atallah F Ahmed; Ming-Hsuan Wu; Guey-Horng Wang; Yang-Chang Wu; Jyh-Horng Sheu
Journal:  J Nat Prod       Date:  2005-07       Impact factor: 4.050

9.  A unified strategy for enantioselective total synthesis of cladiellin and briarellin diterpenes: total synthesis of briarellins E and F and the putative structure of alcyonin and revision of its structure assignment.

Authors:  Olivier Corminboeuf; Larry E Overman; Lewis D Pennington
Journal:  J Org Chem       Date:  2009-08-07       Impact factor: 4.354

10.  Cycloaldol approach to the isobenzofuran core of eunicellin diterpenes.

Authors:  Yonghai Chai; David A Vicic; Matthias C McIntosh
Journal:  Org Lett       Date:  2003-04-03       Impact factor: 6.005

View more
  4 in total

1.  Total syntheses of (+)-vigulariol and (-)-sclerophytin A.

Authors:  Michael T Crimmins; Christina S Stauffer; Mark C Mans
Journal:  Org Lett       Date:  2011-08-19       Impact factor: 6.005

2.  Using (+)-Carvone to access novel derivatives of (+)-ent-Cannabidiol: the first asymmetric syntheses of (+)-ent-CBDP and (+)-ent-CBDV.

Authors:  Alexandra E Golliher; Antonio J Tenorio; Nina O Dimauro; Nicolas R Mairata; F Omar Holguin; William Maio
Journal:  Tetrahedron Lett       Date:  2021-02-05       Impact factor: 2.415

3.  Enantioselective synthesis of (-)-sclerophytin A by a stereoconvergent epoxide hydrolysis.

Authors:  Bin Wang; Armando P Ramirez; Justin J Slade; James P Morken
Journal:  J Am Chem Soc       Date:  2010-10-28       Impact factor: 15.419

Review 4.  Selected Monocyclic Monoterpenes and Their Derivatives as Effective Anticancer Therapeutic Agents.

Authors:  Mariola Zielińska-Błajet; Przemysław Pietrusiak; Joanna Feder-Kubis
Journal:  Int J Mol Sci       Date:  2021-04-30       Impact factor: 5.923

  4 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.