Covalent analogues of DNA base-pairs and triplets. Part 2: synthesis and cytostatic activity of bis(purin-6-yl)acetylenes,-diacetylenes and related compounds

Michal Hocek; Ivan Votruba

doi:10.1016/s0960-894x(02)00077-x

Covalent analogues of DNA base-pairs and triplets. Part 2: synthesis and cytostatic activity of bis(purin-6-yl)acetylenes,-diacetylenes and related compounds

Bioorg Med Chem Lett. 2002 Apr 8;12(7):1055-8. doi: 10.1016/s0960-894x(02)00077-x.

Authors

Michal Hocek¹, Ivan Votruba

Affiliation

¹ Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, CZ-16610 6 Prague, Czech Republic. [email protected]

PMID: 11909716
DOI: 10.1016/s0960-894x(02)00077-x

Abstract

The title bis(purin-6-yl)acetylenes, -diacetylenes, -ethylenes and -ethanes were prepared as covalent base-pair analogues starting from 6-ethynylpurines and 6-iodopurines by cross-coupling and homo-coupling reactions and hydrogenations. The bis(purin-6-yl)acetylenes and -diacetylenes exhibited significant cytostatic activity in vitro (IC(50)=0.4-1.0 micromol/l).

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acetylene / chemical synthesis*
Acetylene / pharmacology
Animals
Antineoplastic Agents / chemical synthesis*
Antineoplastic Agents / pharmacology
Base Pairing*
DNA / chemistry*
DNA / metabolism
Diacetyl / chemistry
Drug Screening Assays, Antitumor
Humans
Mice
Purines / chemistry
Tumor Cells, Cultured / drug effects*

Substances

Antineoplastic Agents
Purines
DNA
Diacetyl
Acetylene
purine