120934-96-5

Usage

Uses

FPL-64176 is a nondihydropyridine Ca2+ channel activator.

Biological Activity

Potent activator of L-type Ca 2+ channels (EC 50 = 16 nM). 40-fold more potent than Bay K 8644 (1,4-Dihydro-2,6-dimethyl-5-nitro-4-[2-(trifluoromethyl)phenyl]-3-pyridinecarboxylic acid, methyl ester ) as a positive inotrope in guinea pig atria.

Biochem/physiol Actions

Potent Ca2+ channel (L-type) activator.

InChI:InChI=1/C22H21NO3/c1-14-19(20(15(2)23-14)22(25)26-3)21(24)18-12-8-7-11-17(18)13-16-9-5-4-6-10-16/h4-12,23H,13H2,1-3H3

Upstream product

• 69687-80-5 methyl 2,5-dimethyl-1H-pyrrole-3-carboxylate 
• 42908-86-1 2-Chloromethylbenzoyl chloride 
• 71-43-2 benzene 
• 10113-29-8 tetrabenzyltin 
• 111596-03-3 methyl 4-(2-iodobenzoyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate 
• 120935-96-8 methyl 2,5-dimethyl-4-<2-(phenylmethyl)benzoyl>-1-<<2-(trimethylsilyl)ethoxy>methyl>-1H-pyrrole-3-carboxylate 
• 154708-63-1 methyl 1-amino-2,5-dimethyl-4-<2-(phenylmethyl)benzoyl>-1H-pyrrole-3-carboxylate 
• 166319-19-3 methyl 4-(2-benzylbenzoyl)-2,5-dimethyl-1-(4-nitrophenethyl)pyrrole-3-carboxylate 
• 32832-95-4 2-benzylbenzaldehyde 
• 166319-10-4 methyl 4-oxo-4-(2-benzylphenyl)-2-butynoate 
• 166319-20-6 methyl 4-hydroxy-4-(2-benzylphenyl)-2-butynoate 
• 4755-81-1 methyl 2-chloroacetoacetate 
• 61608-94-4 1-(2-(phenylmethyl)phenyl)ethanone 
• 55810-66-7 2-(benzyl)benzoyl chloride 

Relevant academic research and scientific papers

Azoalkene route to methyl 2,5-dimethyl-4[2-(phenylmethyl)benzoyl]-1H- pyrrole-3-carboxylate (FPL 64176) and analogues: Synthesis of 1-(BOC- amino)pyrrole-3-carboxylates and their conversion to 1H-pyrroles via 1- aminopyrroles

A new route to the calcium channel activator methyl 2,5-dimethyl-4[2- (phenylmethyl)benzoyl]-1H-pyrrole-3-carboxylate (FPL 64176) and analogues is presented. Reaction of activated diones with BOC-azoalkenes gave pyrroles with the required functionality bu

Discovery and synthesis of methyl 2,5-dimethyl-4-[2- (phenylmethyl)benzoyl]-1H-pyrrole-3-carboxylate (FPL 64176) and analogues: The first examples of a new class of calcium channel activator

Methyl 2,5-dimethyl-4-[2-(phenylmethyl)benzoyl]-1H-pyrrole-3-carboxylate, FPL 64176 (1), is the first example of a new class of calcium channel activator (CCA) that does not act on any of the well-defined calcium channel modulator receptor sites, as typif

A New Synthesis of FPL 64176 and Analogues: The Discovery of Benzoylpyrrole Calcium Channel Activators with Low Nanomolar Potency

Heavy metal assisted halogen displacement on 2-halobenzoylpyrroles (2 and 3) leads to a simple synthesis of FPL 64176 (1) and a variety of analogues (4-10).The difluoro derivative (4), EC 50 1nM, and the amino linked analogue (7), EC 50 2.7nm, are present

An extremely short synthesis of benzoylpyrrole-type calcium channel activators

Friedel-Crafts acylation of methyl 2,5-dimethylpyrrole-3-carboxylate with 2-chloromethylbenzoyl chloride generated the corresponding 4-(2-chloromethylbenzoyl)pyrrole which was reacted in situ with benzene and aluminum chloride to yield the novel calcium c

Pyrrole derivatives, process for their preparation and pharmaceutical compositions containing them

Compounds of formula I, wherein, R1, R2, R3 and R5 have the meanings defined in the specification,G2 represents a chain -(CH2)z(W)y-, in which W has various meanings including C=O, and up to two of the methylene segments in the chain (CH2)zare optionally replaced by -NH- and one segment is optionally replaced by -O- or -(C=NR40)-, and the chain is optionally unsaturated and optionally substituted, and, A is a 5- or 6-membered ring or a bicyclic or tricyclic fused ring system, A being optionally substituted by various substituents,possess useful pharmacological properties, in particular as cardiotonics. Also described are processes for the preparation of compounds of formula I, pharmaceutical compositions containing them and methods of treatment involving their use.