18320-91-7Relevant articles and documents
The meldrum's acid route to prodigiosin analogues
Hunter, Gordon A.,McNab, Hamish,Withell, Kirsti
, p. 1707 - 1711 (2010)
3-Methoxy-5-(2-thienyl)thiophene-2-carboxaldehyde and 3-methoxy-l-methyl-5- (2-thienyl)pyrrole-2-carboxaldehyde were prepared from the appropriate 3-hydroxypyrrole or 3-hydroxythiophene by regioselective O-alkylation and formylation. Condensation of these
Total Synthesis and Antimalarial Activity of 2-(p-Hydroxybenzyl)-prodigiosins, Isoheptylprodigiosin, and Geometric Isomers of Tambjamine MYP1 Isolated from Marine Bacteria
Kancharla, Papireddy,Li, Yuexin,Yeluguri, Monish,Dodean, Rozalia A.,Reynolds, Kevin A.,Kelly, Jane X.
, p. 8739 - 8754 (2021/06/30)
Highly efficient and straightforward synthetic routes toward the first total synthesis of 2-(p-hydroxybenzyl)-prodigiosins (2-5), isoheptylprodigiosin (6), and geometric isomers of tambjamine MYP1 ((E/Z)-7) have been developed. The crucial steps involved in these synthetic routes are the construction of methoxy-bipyrrole-carboxaldehydes (MBCs) and a 20-membered macrocyclic core and a regioselective demethylation of MBC analogues. These new synthetic routes enabled us to generate several natural prodiginines24-27in larger quantity. All of the synthesized natural products exhibited potent asexual blood-stage antiplasmodial activity at low nanomolar concentrations against a panel ofPlasmodium falciparumparasites, with a great therapeutic index. Notably, prodiginines6and24-27provided curative in vivo efficacy against erythrocyticPlasmodium yoeliiat 25 mg/kg × 4 days via oral route in a murine model. No overt clinical toxicity or behavioral change was observed in any mice treated with prodiginines and tambjamines.
Intermolecular dearomatization reaction of pyrroles promoted by silica gel
Zhou, Yong,Zhuo, Chun-Xiang,Gu, Qing,You, Shu-Li
supporting information, p. 912 - 916 (2015/03/30)
An efficient synthesis of polysubstituted 2H-pyrrole derivatives via a silica gel-promoted intermolecular dearomative Michael addition of pyrroles with α,β-unsaturated ketones has been developed. This transformation features environmentally benign promoter, high efficiency, wide substrate scope and mild reaction conditions.
Total Synthesis of Prodigiosin, Prodigiosene, and Desmethoxyprodigiosin: Diels-Adler Reactions of Heterocyclic Azadienes and Development of an Effective Palladium(II)-Promoted 2,2'-Bipyrrole Coupling Procedure
Boger, Dale L.,Patel, Mona
, p. 1405 - 1415 (2007/10/02)
The total synthesis of prodigiosin (1), a red pigment first isolated from Serratia marcescens, possessing the characteristic pyrrolylpyrromethene skeleton of a class of naturally occurring polypyrroles exhibiting antimicrobial and cytotoxic properties, is detailed.The approach is based application of an inverse electron demand Diels-Adler reaction of dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate in a 1,2,4,5-tetrazine--->1,2-diazine--->pyrrole strategy for preparation of prodigiosin pyrrole ring B and the subsequent implementation of an effective intramolecular palladium(II)-promoted 2,2'-diaryl coupling for construction of the prodigiosin 2,2'-bipyrrole AB ring system.In situ generated activated ester derivatives of pyrrole-1-carboxylic acid or the use of pyrrole-1-carboxylic acid anhydride proved suitable for the generation of mixed 1,1'-carbonyldipyrrole compounds for use in the palladium(II)-promoted mixed, 2,2'-bipyrrole coupling.Extensions of this approach to the preparation of the naturally occurring parent pyrrolylpyrromethene, prodigiosene (2a), and 2-methyl-3-pentylprodigiosene (2e, desmethoxyprodigiosin) are detailed.A comparison of the in vitro cytotoxic properties of prodigiosin (1), prodigiosene (2a), and 2-methyl-3-pentylprodigiosene (2e) are reported and reveal exceptional cytotoxic potency (3.7*10-4 μg/mL = 3.7*10-10 g/mL) for prodigiosin against 9PS (P388) mouse leukemia which may be attributed to the presence of the prodigiosin C-6 methoxy substituent.
PYRROLES FROM KETOXIMES AND ACETYLENE. 29. SYNTHESIS OF ALKYLPYRROLES FROM DIALKYLKETOXIMES AND DICHLOROETHANE BY REACTION WITH KOH-DMSO
Trofimov, B. A.,Mikhaleva, A. I.,Vasil'ev, A. N.,Korostova, S. E.,Shevchenko, S. G.
, p. 46 - 49 (2007/10/02)
Treatment of dialkylketoximes with dichloroethane and KOH-DMSO results in the formation of alkylpyrroles in 31-61percent yields.In addition, the corresponding 1-vinylpyrroles are formed simultaneously in yields up to 18percent.The corresponding 1,2-bis(alkylideneiminoxy)ethanes are obtained as side products in the reaction; they result from nucleophilic displacement of chlorine atoms by oximate anions.
