PMID- 19731594 OWN - NLM STAT- MEDLINE DCOM- 20090929 LR - 20090907 IS - 1934-578X (Print) IS - 1555-9475 (Linking) VI - 4 IP - 7 DP - 2009 Jul TI - Synthesis of neolamellarin A, an inhibitor of hypoxia-inducible factor-1. PG - 925-6 AB - Neolamellarin A, a metabolite isolated from the sponge Dendrilla nigra, was found to inhibit hypoxia-inducible factor-1 (HIF-1) activation by 26% at 10 microM concentration and inhibition of HIF-1 has become a major antitumor molecular target. Herein the first synthesis of neolamellarin A is described. The synthetic strategy features the condensation of vinylogous amide with aminomalonate to construct the 3,4-bis(4-methoxyphenyl)-1H-pyrrole core and the subsequent acylation and deprotection rendered the target compound in 18% over all yield. FAU - Arafeh, Khaled M AU - Arafeh KM AD - Chemistry Department, King Fahd University of Petroleum and Minerals, Dhahran 31261, Saudi Arabia. FAU - Ullah, Nisar AU - Ullah N LA - eng PT - Journal Article PL - United States TA - Nat Prod Commun JT - Natural product communications JID - 101477873 RN - 0 (Amides) RN - 0 (Hypoxia-Inducible Factor 1) RN - 0 (Indicators and Reagents) RN - 0 (Pyrroles) RN - 0 (neolamellarin A) SB - IM MH - Acylation MH - Amides/chemistry MH - Animals MH - Hypoxia-Inducible Factor 1/*antagonists & inhibitors MH - Indicators and Reagents MH - Porifera/chemistry MH - Pyrroles EDAT- 2009/09/08 06:00 MHDA- 2009/09/30 06:00 CRDT- 2009/09/08 06:00 PHST- 2009/09/08 06:00 [entrez] PHST- 2009/09/08 06:00 [pubmed] PHST- 2009/09/30 06:00 [medline] PST - ppublish SO - Nat Prod Commun. 2009 Jul;4(7):925-6.