120555-31-9

Basic information

• Product Name: (2E,4E)-5-(4-methoxyphenyl)-N-[(2R)-5-pyridin-3-ylpentan-2-yl]deca-2,4 -dienamide
• Synonyms: (2E,4E)-5-(4-methoxyphenyl)-N-[(2R)-5-pyridin-3-ylpentan-2-yl]deca-2,4 -dienamide;Ro 24-0238;(2E,4E)-5-(4-Methoxyphenyl)-N-[(R)-1-methyl-4-(3-pyridinyl)butyl]-2,4-decadienamide
• CAS NO: 120555-31-9
• Molecular Formula: C₂₇H₃₆N₂O₂
• Molecular Weight: 420.59
• Mol File: 120555-31-9.mol

Chemical Properties

• Melting Point: 88-89 °C(Solv: ethyl ether (60-29-7); hexane (110-54-3))
• Boiling Point: 627.1°Cat760mmHg
• Flash Point: 333.1°C
• Appearance: /
• Density: 1.026g/cm³
• Vapor Pressure: 1.21E-15mmHg at 25°C
• Refractive Index: 1.543
• PKA: 14.07±0.46(Predicted)
• CAS DataBase Reference: (2E,4E)-5-(4-methoxyphenyl)-N-[(2R)-5-pyridin-3-ylpentan-2-yl]deca-2,4 -dienamide(CAS DataBase Reference)
• NIST Chemistry Reference: (2E,4E)-5-(4-methoxyphenyl)-N-[(2R)-5-pyridin-3-ylpentan-2-yl]deca-2,4 -dienamide(120555-31-9)
• EPA Substance Registry System: (2E,4E)-5-(4-methoxyphenyl)-N-[(2R)-5-pyridin-3-ylpentan-2-yl]deca-2,4 -dienamide(120555-31-9)

Safety Data

• Hazardous Substances Data: 120555-31-9(Hazardous Substances Data)

Usage

General Description

The chemical compound (2E,4E)-5-(4-methoxyphenyl)-N-[(2R)-5-pyridin-3-ylpentan-2-yl]deca-2,4-dienamide is a synthetic compound with a complex molecular structure. It is a combination of a 2,4-dienamide and a pyridinylpentan-2-yl group, both of which are linked to a 4-methoxyphenyl group. (2E,4E)-5-(4-methoxyphenyl)-N-[(2R)-5-pyridin-3-ylpentan-2-yl]deca-2,4 -dienamide has potential applications in the pharmaceutical industry, possibly as a ligand for biological receptors or as a precursor for the synthesis of other compounds with therapeutic properties. Its specific molecular structure and potential biological activity make it an interesting target for further research and development.

InChI:InChI=1/C27H36N2O2/c1-4-5-6-13-24(25-16-18-26(31-3)19-17-25)14-8-15-27(30)29-22(2)10-7-11-23-12-9-20-28-21-23/h8-9,12,14-22H,4-7,10-11,13H2,1-3H3,(H,29,30)/b15-8+,24-14+/t22-/m1/s1

Upstream product

• 111954-72-4 (R)-α-methyl-3-pyridinebutanamine 
• 120554-77-0 (E,E)-5-(4-methoxyphenyl)-2,4-decadienoic acid 4-nitrophenyl ester 
• 152613-95-1 (R)-3-(4-azidopentyl)pyridine 
• 120554-38-3 (E,E)-5-(4-methoxyphenyl)-2,4-decadienoic acid 
• 142-61-0 Hexanoyl chloride 
• 100-66-3 methoxybenzene 
• 119981-04-3 alpha-methyl-3-pyridinebutanol 
• 152613-94-0 (S)-α-methyl-3-pyridinebutanol methanesulfonate 
• 120554-78-1 (2E,4Z)-5-(4-methoxyphenyl)-2,4-decadienoic acid 4-nitrophenyl ester 
• 120556-12-9 (R,S)-3-hydroxy-3-(4-methoxyphenyl)octanenitrile 
• 6397-82-6 4'-methoxyhexanophenone 
• 152613-93-9 (S)-α-methyl-3-pyridinebutyl butyrate 
• 152533-15-8 (R,S)-α-methyl-3-pyridinebutyl butyrate 
• 152613-92-8 (S)-α-methyl-3-pyridinebutyl acetate 

Relevant articles and documents

SYNTHESIS OF AN ORALLY ACTIVE PAF ANTAGONIST OF THE N-PENTADIENAMIDE CLASS

The PAF antagonist -5-(4-methoxyphenyl)-N--2,4-decadienamide (2) was synthesized from (S)-α-methyl-3-pyridinebutanol (14), which was obtained either from ethyl lactate or by enantioselective kinetic hydrolysis of its racemate using the lipase derived from Pseudomonas cepacia (syn.P. fluorescens).Mesylation of 14, followed by azide displacement and hydrogenation, produced amine (7), which was coupled with the p-nitrophenol ester (8) to give 2.The direct coupling of (E,E)-5-(4-methoxyphenyl)-2,4-decadienoic acid (27) with azide(24) in the presence of tri-n-butylphosphine also gave 2.Acid (27) was prepared by a vinylogous Reformatsky reaction between ketone (25) and methyl 4-bromocrotonate.

Pentadienyl carboxamide derivatives as antagonists of platelet-activating factor

A series of N-[4-(3-pyridinyl)butyl]-5,5-disubstituted-pentadienamides was prepared and evaluated for PAF-antagonist activity. Compounds were assayed in vitro in a PAF-binding assay employing washed, whole dog platelets as the receptor source and in vivo after intravenous or oral administration for their ability to prevent PAF-induced bronchoconstriction in guinea pigs. Criteria required for good oral activity in the latter model include an (E,E)-5-phenyl-2,4-pentadienamide, a second phenyl or a four- or five-carbon alkyl moiety in the 5-position of the diene, and an (R)-[1-alkyl-4-(3-pyridinyl)butyl] substituent on the carboxamide nitrogen atom. The alkyl substituent on this side chain can be methyl, ethyl, or cyclopropyl. Two members of this series, [R-(E)]-5,5-bis(4-methoxyphenyl)-N-[1-methyl-4-(3-pyridinyl)butyl]-2,4- pentadienamide (31) and [R-(E,E)]-5-(4-methoxyphenyl)-N-[1-methyl-4-(3-pyridinyl)butyl]-2,4- decadienamide (58), were selected for further pharmacological evaluation. Both were found to be substantially longer acting after oral administration than the corresponding S enantiomers in the guinea pig bronchoconstriction assay. A second in vivo model used to evaluate PAF antagonists determines the ability of test compounds to decrease the area of skin wheals induced by an intradermal injection of PAF. In this model, using both rats and guinea pigs, compounds 31 and 58 were found to be as active as the reference PAF antagonist 3-[4-(2-chlorophenyl)-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3- a][1,4]diazepin-2-yl]-1-(4-morpholinyl)-1-propanone (45).

Pentadieneamides

Compounds of the formula STR1 Y is O ir S, *A is paraphenylene or *----(CH2)n----(X)m --(CH2)r ----, X is O, S or --CH=CH--, n or r, independently, are integers from 0 to 3, s is an integer from 0 to 1, m is an integer from 0 to 1, provided that when m is 1, n+s must be at least 2, R1 and R2, independently, are hydrogen, lower alkyl, cycloalkyl, lower alkenyl, Het, aryl, R3, R4 and R8, independently, are hydrogen, lower alkyl, aryl, R5 and R6, independently, are hydrogen or lower alkyl, R7 is hydrogen, lower alkyl, cycloalkyl, Het-lower alkyl or aryl, Het is a monocyclic 5- or 6-membered hetero aromatic or a bicyclic heteroaromatic radical containing one or two hetero atoms selected from nitrogen, oxygen and sulfur, which radical may be substituted by lower alkyl, halogen or aryl, and the asterisk denotes the point of attachment, and when R6 and R7 are different, their enantiomers and racemic mixtures thereof, when R1 and R2 are different, their geometric isomers, and pharmaceutically acceptable acid addition salts thereof, are described. The compounds of formula I exhibit activity as platelet activating factor (PAF) antagonists and are, therefore, useful in disease states characerized by excess platelet activating factor or for the prevention and treatment of cardiovascular disease, pulmonary diseases, immunological disorders, inflammatory diseases, dermatological disorders, shock or transplant rejection.