86688-93-9Relevant articles and documents
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.
Magnesiation of N-Heterocycles Using i-PrMgCl · LiCl and catalytic diisopropylamine
Nxumalo,Dinsmore
supporting information, p. 2478 - 2484 (2015/11/10)
The direct magnesiation of various N-heterocyclic compounds with i-PrMgCl · LiCl and catalytic diisopropylamine allows for preparation of 2-substituted pyrroles, imidazole, indoles, and benzimidazoles, in moderate to good yields. The magnesiated substrates canreadily undergo a Kumada-type coupling with iodo-aryls in the presence of catalytic Pd(PPh3)4.
Magnesiation Employing Grignard Reagents and Catalytic Amine. Application to the Functionalization of N-Phenylsulfonylpyrrole
Dinsmore, Andrew,Billing, David G.,Mandy, Karen,Michael, Joseph P.,Mogano, Daniel,Patil, Shivaputra
, p. 293 - 296 (2007/10/03)
(Matrix presented) N-Phenylsulfonylpyrrole 1 is magnesiated by treatment with isopropylmagnesium chloride and catalytic diisopropylamine. Reaction with various electrophiles, including palladium-catalyzed aryl- and heteroaryl cross-coupling, provides 2-su
