138258-37-4

Basic information

• Product Name: Bicyclo[2.2.1]heptan-2-amine, 3-(2-propenyl)-, (2-endo,3-exo)-(+)- (9CI)
• Synonyms: Bicyclo[2.2.1]heptan-2-amine, 3-(2-propenyl)-, (2-endo,3-exo)-(+)- (9CI)
• CAS NO: 138258-37-4
• Molecular Formula: C10H17N
• Molecular Weight: 151.24868
• Product Categories: CYCLOPENTANE
• Mol File: 138258-37-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Bicyclo[2.2.1]heptan-2-amine, 3-(2-propenyl)-, (2-endo,3-exo)-(+)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Bicyclo[2.2.1]heptan-2-amine, 3-(2-propenyl)-, (2-endo,3-exo)-(+)- (9CI)(138258-37-4)
• EPA Substance Registry System: Bicyclo[2.2.1]heptan-2-amine, 3-(2-propenyl)-, (2-endo,3-exo)-(+)- (9CI)(138258-37-4)

Safety Data

• Hazardous Substances Data: 138258-37-4(Hazardous Substances Data)

Upstream product

• 149575-35-9 (1R,3R,4S)-3-Allyl-bicyclo[2.2.1]heptan-2-one 
• 149575-33-7 (+)-exo-3-(2-propenyl)-bicyclo[2.2.1]heptan-2-one 
• 187030-58-6 (1S,3S,4R)-3-Allyl-bicyclo[2.2.1]heptan-2-one oxime 
• 75040-20-9 exo-3-allylnorcamphor 

Relevant articles and documents

Improved synthesis of (5Z)-7-3-endo-{(benzenesulfonamido)-bicyclo[2.2.1]heptyl}hept-5-enoic acid (S-145) derivatives and their iodine-125-labeled radioligands for the study of thromboxane A2 receptor

An improved synthetic scheme for (5Z)-7-{3-endo-[(benzenesulfonamido)-bicyclo[2.2.1]heptyl}-hept-5-enoic acid (S145) and its analogs has been designed. The procedure involves direct sulfonylation of 2-allyl-3-aminobicyclo[2.2.1]heptane intermediate followed by ozonolysis and addition of a C5 carboxyl unit. The yield of the final product was significantly improved. (5Z)-7-{3-endo-[(4-iodobenzensulfonamido)-bicyclo [2.2.1]heptyl}hept-5-enoic acid (HS-145) and (5Z)-7-{3-endo-[(4-hydroxy-benzensulfonamido)-bicyclo [2.2.1]heptyl}hept-5-enoic acid (HS-145) were synthesized directly without any protection and deprotection steps. [125I](5Z)-7-{3-endo-[(4-iodobenzensulfonamido)- bicyclo[2.2.1]heptyl}hept-5-enoic acid ([125I]HS-145) was prepared from IS-145 through an organotin intermediate and [125I]sodium iodide with high specific radioactivity and good recovery of radioactivity. [125I](5Z)-7-{3-endo-[(4-hydroxy 3-iodo-benzensulfonamido)-bicyclo[2.2.1]-heptyl}hept-5-enoic acid ([125I]HS-145) was prepared by direct iodination with sodium iodide using a modified chloramine-T method. Both [125]HS-145 and [125I]HS-145 were found to be valuable radioligands for studying thromboxane A2 (TXA2) receptor.

Synthesis and in Vitro Activity of Various Derivatives of a Novel Thromboxane Receptor Antagonist, (+/-)-(5Z)-7-bicyclohept-2-exo-yl>heptenoic Acid

Several sulfonyl derivatives (13a-t) of (+/-)-(5Z)-7-(3-endo-amonobicyclohept-2-exo-yl)heptenoic acid (VI) were synthesized via its methyl ester 10.Sulfonylation of 10 with 11a-t followed by saponification yielded 13a-t.Inhibitory concentrations (IC50) of the corresponding sodium salts 14a-t for platelet aggregation were measured with rat washed platelets (WP) and rabbit platelet-rich plasma (PRP).IC50 values of some derivatives for contraction of the rat aorta were also measured.The IC50 values for rat WP increased from 2.9 to 26 nM in the order of 14a, 14c, 14d, and 14b for derivatives with an arylsulfonyl residue, depending on the number of interventing methylene groups.Methyl derivative 14e exhibited a higher IC50 value than n-hexyl derivative 14f.Substitution with a p-methyl-, p-fluoro-, or p-chloro group in 14a retained or slightly reduced its IC50 value, while a p-n-pentyl or p-oxycarbonyl group augmented it significantly.The representative 14a supressed (15S)-15-hydroxy-11,9-(epoxymethano)prosta-5(Z),13(E)-dienoic acid (U-46619) induced aggregation of human WP with an IC50 value of 7.7 nM, which corresponds well to the IC50 value of 3 nM obtained for each displacement by 14a of -U-46619 or (5Z,15ξ)-9α,11α-(dimethylmethano)-15-hydroxy-16-(3-iodo-4-hydroxyphenyl)-17,18,19,20-tetranor-13-aza-11a-carbathrombo-5-enoic acid (-PTA-OH) bound to human WP.Synthesis of thromboxane A2 (TxA2) in human WP stimulated by thrombin was not inhibited by 14a at a concentration up to 10 μM.From these observations, the corresponding acid 13a (S-145) was concluded to be potent TxA2 receptor antagonist.