120934-96-5

Basic information

• Product Name: FPL 64176
• Synonyms: FPL 64176;2,5-DIMETHYL-4-[2-(PHENYLMETHYL)BENZOYL]-1H-PYRROLE-3-CARBOXLIC ACID METHYL ESTER;2,5-DIMETHYL-4-[2-(PHENYLMETHYL)BENZOYL]-1H-PYRROLE-3-CARBOXYLIC ACID METHYL ESTER;FPL 64176 >94% POTENT CA2+ CHANNEL (;2,5-Dimethyl-4-(2-benzylbenzoyl)-1H-pyrrole-3-carboxylic acid methyl ester;4-(2-Benzylbenzoyl)-2,5-dimethyl-1H-pyrrole-3-carboxylic acid methyl ester;MDMWHKZANMNXTF-UHFFFAOYSA-N
• CAS NO: 120934-96-5
• Molecular Formula: C₂₂H₂₁NO₃
• Molecular Weight: 347.41
• Product Categories: Calcium channel
• Mol File: 120934-96-5.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 547.8°Cat760mmHg
• Flash Point: 285.1°C
• Appearance: tan/solid
• Density: 1.174g/cm³
• Vapor Pressure: 4.72E-12mmHg at 25°C
• Refractive Index: 1.6
• Storage Temp.: 2-8°C
• Solubility: DMSO: 10 mg/mL Solutions should be freshly prepared.
• CAS DataBase Reference: FPL 64176(CAS DataBase Reference)
• NIST Chemistry Reference: FPL 64176(120934-96-5)
• EPA Substance Registry System: FPL 64176(120934-96-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 120934-96-5(Hazardous Substances Data)

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

• 10113-29-8 tetrabenzyltin 
• 111596-03-3 methyl 4-(2-iodobenzoyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate 
• 61608-94-4 1-(2-(phenylmethyl)phenyl)ethanone 
• 55810-66-7 2-(benzyl)benzoyl chloride 
• 120935-96-8 methyl 2,5-dimethyl-4-<2-(phenylmethyl)benzoyl>-1-<<2-(trimethylsilyl)ethoxy>methyl>-1H-pyrrole-3-carboxylate 
• 120935-95-7 methyl 4-bromo-2,5-dimethyl-1-<<2-(trimethylsilyl)ethoxy>methyl>-1H-pyrrole-3-carboxylate 
• 120935-94-6 methyl 4-bromo-2,5-dimethyl-1H-pyrrole-3-carboxylate 
• 69687-80-5 methyl 2,5-dimethyl-1H-pyrrole-3-carboxylate 
• 154708-57-3 methyl 1-tert-butoxycarbonylamino-2,5-dimethyl-4-<2-(phenylmethyl)benzoyl>-1H-pyrrole-3-carboxylate 
• 120935-81-1 1-<2-(phenylmethyl)benzoyl>-1,3-butanedione 
• 950203-40-4 methyl 3-tert-butoxycarbonylazo-2-butenoate 
• 4755-81-1 methyl 2-chloroacetoacetate 
• 166319-20-6 methyl 4-hydroxy-4-(2-benzylphenyl)-2-butynoate 
• 166319-10-4 methyl 4-oxo-4-(2-benzylphenyl)-2-butynoate 

Relevant articles and documents

Synthesis of FPL 64176 by 1,3-Dipolar Cycloaddition

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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

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