Design, synthesis, and evaluation of carbamate-substituted analogues of (+)-discodermolide

Amos B. Smith, B. Scott Freeze, Matthew J. LaMarche, Tomoyasu Hirose, Ignacio Brouard, Paul V. Rucker, Ming Xian, Kurt F. Sundermann, Simon J. Shaw, Mark A. Burlingame, Susan Band Horwitz, David C. Myles

Research output: Contribution to journalArticle

40 Citations (Scopus)

Abstract

(Chemical Equation Presented) The design, syntheses, and biological evaluation of 22 totally synthetic analogues of the potent microtubule- stabilizing agent (+)-discodermolide (1) have been achieved. Structure-activity relationships of the C(19) carbamate were defined, exploiting two synthetically simplified scaffolds, as well as the parent (+)-discodermolide framework.

Original languageEnglish (US)
Pages (from-to)311-314
Number of pages4
JournalOrganic Letters
Volume7
Issue number2
StatePublished - Jan 20 2005

Fingerprint

Carbamates
analogs
evaluation
Excipients
Structure-Activity Relationship
synthesis
Scaffolds
Microtubules
discodermolide

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Smith, A. B., Freeze, B. S., LaMarche, M. J., Hirose, T., Brouard, I., Rucker, P. V., ... Myles, D. C. (2005). Design, synthesis, and evaluation of carbamate-substituted analogues of (+)-discodermolide. Organic Letters, 7(2), 311-314.

Design, synthesis, and evaluation of carbamate-substituted analogues of (+)-discodermolide. / Smith, Amos B.; Freeze, B. Scott; LaMarche, Matthew J.; Hirose, Tomoyasu; Brouard, Ignacio; Rucker, Paul V.; Xian, Ming; Sundermann, Kurt F.; Shaw, Simon J.; Burlingame, Mark A.; Band Horwitz, Susan; Myles, David C.

In: Organic Letters, Vol. 7, No. 2, 20.01.2005, p. 311-314.

Research output: Contribution to journalArticle

Smith, AB, Freeze, BS, LaMarche, MJ, Hirose, T, Brouard, I, Rucker, PV, Xian, M, Sundermann, KF, Shaw, SJ, Burlingame, MA, Band Horwitz, S & Myles, DC 2005, 'Design, synthesis, and evaluation of carbamate-substituted analogues of (+)-discodermolide', Organic Letters, vol. 7, no. 2, pp. 311-314.
Smith AB, Freeze BS, LaMarche MJ, Hirose T, Brouard I, Rucker PV et al. Design, synthesis, and evaluation of carbamate-substituted analogues of (+)-discodermolide. Organic Letters. 2005 Jan 20;7(2):311-314.
Smith, Amos B. ; Freeze, B. Scott ; LaMarche, Matthew J. ; Hirose, Tomoyasu ; Brouard, Ignacio ; Rucker, Paul V. ; Xian, Ming ; Sundermann, Kurt F. ; Shaw, Simon J. ; Burlingame, Mark A. ; Band Horwitz, Susan ; Myles, David C. / Design, synthesis, and evaluation of carbamate-substituted analogues of (+)-discodermolide. In: Organic Letters. 2005 ; Vol. 7, No. 2. pp. 311-314.
@article{4e6bde6a0221479fa63242de816b2b4e,
title = "Design, synthesis, and evaluation of carbamate-substituted analogues of (+)-discodermolide",
abstract = "(Chemical Equation Presented) The design, syntheses, and biological evaluation of 22 totally synthetic analogues of the potent microtubule- stabilizing agent (+)-discodermolide (1) have been achieved. Structure-activity relationships of the C(19) carbamate were defined, exploiting two synthetically simplified scaffolds, as well as the parent (+)-discodermolide framework.",
author = "Smith, {Amos B.} and Freeze, {B. Scott} and LaMarche, {Matthew J.} and Tomoyasu Hirose and Ignacio Brouard and Rucker, {Paul V.} and Ming Xian and Sundermann, {Kurt F.} and Shaw, {Simon J.} and Burlingame, {Mark A.} and {Band Horwitz}, Susan and Myles, {David C.}",
year = "2005",
month = "1",
day = "20",
language = "English (US)",
volume = "7",
pages = "311--314",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "2",

}

TY - JOUR

T1 - Design, synthesis, and evaluation of carbamate-substituted analogues of (+)-discodermolide

AU - Smith, Amos B.

AU - Freeze, B. Scott

AU - LaMarche, Matthew J.

AU - Hirose, Tomoyasu

AU - Brouard, Ignacio

AU - Rucker, Paul V.

AU - Xian, Ming

AU - Sundermann, Kurt F.

AU - Shaw, Simon J.

AU - Burlingame, Mark A.

AU - Band Horwitz, Susan

AU - Myles, David C.

PY - 2005/1/20

Y1 - 2005/1/20

N2 - (Chemical Equation Presented) The design, syntheses, and biological evaluation of 22 totally synthetic analogues of the potent microtubule- stabilizing agent (+)-discodermolide (1) have been achieved. Structure-activity relationships of the C(19) carbamate were defined, exploiting two synthetically simplified scaffolds, as well as the parent (+)-discodermolide framework.

AB - (Chemical Equation Presented) The design, syntheses, and biological evaluation of 22 totally synthetic analogues of the potent microtubule- stabilizing agent (+)-discodermolide (1) have been achieved. Structure-activity relationships of the C(19) carbamate were defined, exploiting two synthetically simplified scaffolds, as well as the parent (+)-discodermolide framework.

UR - http://www.scopus.com/inward/record.url?scp=13444291392&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=13444291392&partnerID=8YFLogxK

M3 - Article

VL - 7

SP - 311

EP - 314

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 2

ER -