Antineoplastic agents 463. Synthesis of combretastatin A-3 diphosphate prodrugs

George Pettit, M. D. Minardi, M. R. Boyd, Robin Pettit

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

A new and more efficient synthesis of combretastatin A-3 (2a) was completed (8.4% overall yield) starting from methyl gallate and isovanillin with aldehyde 5 and phosphonium salt 8 as key intermediates. Conversion of combretastatin A-3 (2a) to a series of diphosphate prodrugs (10a-1) was readily achieved. Both the diphosphate sodium (10a) and potassium salts (10c) displayed aqueous solubility in excess of 220 mg/ml at room temperature and good cancer cell line inhibitory activity.

Original languageEnglish (US)
Pages (from-to)397-403
Number of pages7
JournalAnti-Cancer Drug Design
Volume15
Issue number6
StatePublished - 2000

Fingerprint

Diphosphates
Prodrugs
Antineoplastic Agents
Salts
Aldehydes
Solubility
Potassium
Cells
Cell Line
Temperature
Neoplasms
combretastatin A3
methyl gallate
isovanillin
sodium pyrophosphate

Keywords

  • Cation salts
  • Combretastatin A-3
  • Diphosphate
  • Prodrugs

ASJC Scopus subject areas

  • Drug Discovery
  • Organic Chemistry
  • Oncology
  • Biochemistry, Genetics and Molecular Biology(all)
  • Biochemistry
  • Pharmacology

Cite this

Antineoplastic agents 463. Synthesis of combretastatin A-3 diphosphate prodrugs. / Pettit, George; Minardi, M. D.; Boyd, M. R.; Pettit, Robin.

In: Anti-Cancer Drug Design, Vol. 15, No. 6, 2000, p. 397-403.

Research output: Contribution to journalArticle

@article{7851cd2b44974c37aa3587b27e14a45f,
title = "Antineoplastic agents 463. Synthesis of combretastatin A-3 diphosphate prodrugs",
abstract = "A new and more efficient synthesis of combretastatin A-3 (2a) was completed (8.4{\%} overall yield) starting from methyl gallate and isovanillin with aldehyde 5 and phosphonium salt 8 as key intermediates. Conversion of combretastatin A-3 (2a) to a series of diphosphate prodrugs (10a-1) was readily achieved. Both the diphosphate sodium (10a) and potassium salts (10c) displayed aqueous solubility in excess of 220 mg/ml at room temperature and good cancer cell line inhibitory activity.",
keywords = "Cation salts, Combretastatin A-3, Diphosphate, Prodrugs",
author = "George Pettit and Minardi, {M. D.} and Boyd, {M. R.} and Robin Pettit",
year = "2000",
language = "English (US)",
volume = "15",
pages = "397--403",
journal = "Anti-Cancer Drug Design",
issn = "0266-9536",
publisher = "Cognizant Communication Corporation",
number = "6",

}

TY - JOUR

T1 - Antineoplastic agents 463. Synthesis of combretastatin A-3 diphosphate prodrugs

AU - Pettit, George

AU - Minardi, M. D.

AU - Boyd, M. R.

AU - Pettit, Robin

PY - 2000

Y1 - 2000

N2 - A new and more efficient synthesis of combretastatin A-3 (2a) was completed (8.4% overall yield) starting from methyl gallate and isovanillin with aldehyde 5 and phosphonium salt 8 as key intermediates. Conversion of combretastatin A-3 (2a) to a series of diphosphate prodrugs (10a-1) was readily achieved. Both the diphosphate sodium (10a) and potassium salts (10c) displayed aqueous solubility in excess of 220 mg/ml at room temperature and good cancer cell line inhibitory activity.

AB - A new and more efficient synthesis of combretastatin A-3 (2a) was completed (8.4% overall yield) starting from methyl gallate and isovanillin with aldehyde 5 and phosphonium salt 8 as key intermediates. Conversion of combretastatin A-3 (2a) to a series of diphosphate prodrugs (10a-1) was readily achieved. Both the diphosphate sodium (10a) and potassium salts (10c) displayed aqueous solubility in excess of 220 mg/ml at room temperature and good cancer cell line inhibitory activity.

KW - Cation salts

KW - Combretastatin A-3

KW - Diphosphate

KW - Prodrugs

UR - http://www.scopus.com/inward/record.url?scp=0034434231&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0034434231&partnerID=8YFLogxK

M3 - Article

VL - 15

SP - 397

EP - 403

JO - Anti-Cancer Drug Design

JF - Anti-Cancer Drug Design

SN - 0266-9536

IS - 6

ER -