835916-36-4

Basic information

• Product Name: N-[(2S,5S,8R,12R)-5,8-Dibenzyl-2-(1H-indol-3-ylmethyl)-3,6,11,14-tetraoxo-1,4,7,10-tetraaza-cyclotetradec-12-yl]-succinamic acid
• Synonyms: N-[(2S,5S,8R,12R)-5,8-Dibenzyl-2-(1H-indol-3-ylmethyl)-3,6,11,14-tetraoxo-1,4,7,10-tetraaza-cyclotetradec-12-yl]-succinamic acid
• CAS NO: 835916-36-4
• Molecular Weight: 680.761
• Mol File: 835916-36-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: N-[(2S,5S,8R,12R)-5,8-Dibenzyl-2-(1H-indol-3-ylmethyl)-3,6,11,14-tetraoxo-1,4,7,10-tetraaza-cyclotetradec-12-yl]-succinamic acid(CAS DataBase Reference)
• NIST Chemistry Reference: N-[(2S,5S,8R,12R)-5,8-Dibenzyl-2-(1H-indol-3-ylmethyl)-3,6,11,14-tetraoxo-1,4,7,10-tetraaza-cyclotetradec-12-yl]-succinamic acid(835916-36-4)
• EPA Substance Registry System: N-[(2S,5S,8R,12R)-5,8-Dibenzyl-2-(1H-indol-3-ylmethyl)-3,6,11,14-tetraoxo-1,4,7,10-tetraaza-cyclotetradec-12-yl]-succinamic acid(835916-36-4)

Safety Data

• Hazardous Substances Data: 835916-36-4(Hazardous Substances Data)

Upstream product

• 108-30-5 succinic acid anhydride 
• 211689-26-8 (12R)-amino-(5S,8R)-dibenzyl-2-(S)-(1H-indol-3-ylmethyl)-1,4,7,10-tetraaza-cyclotetradecane-3,6,11,14-tetraone 
• 258530-41-5 N-[1-{1-[1-(benzyloxycarbonylamino-methyl)-2-phenyl-ethylcarbamoyl]-2-phenyl-ethylcarbamoyl}-2-(1H-indol-3-yl)-ethyl]-2-tert-butoxycarbonylamino-succinamic acid benzyl ester 
• 258530-42-6 N-[1-(S)-[1-(S)-(2-amino-1-(R)-benzylethylcarbamoyl)-2-phenylethylcarbamoyl]-2-(1H-indol-3-yl)ethyl]-2-(R)-tert-butoxycarbonylaminosuccinic acid 
• 258530-43-7 [(2S,5S,8R,12R)-5,8-Dibenzyl-2-(1H-indol-3-ylmethyl)-3,6,11,14-tetraoxo-1,4,7,10-tetraaza-cyclotetradec-12-yl]-carbamic acid tert-butyl ester 
• 334942-04-0 [(R)-2-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionylamino)-3-phenyl-propyl]-carbamic acid benzyl ester 
• 835916-04-6 (2-tert-butoxycarbonylamino-3-phenyl-propyl)-carbamic acid benzyl ester 
• 211689-63-3 (2-{2-[2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-3-phenyl-propionylamino}-3-phenyl-propyl)-carbamic acid benzyl ester 
• 211689-64-4 (2-(R)-{2-(S)-[2-(S)-amino-3-(1H-indol-3-yl)propionylamino]-3-phenylpropionylamino}-3-phenylpropyl)carbamic acid benzyl ester 
• 185384-16-1 (2R)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropylamine 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 

Relevant articles and documents

Insertion of an aspartic acid moiety into cyclic pseudopeptides: Synthesis and biological characterization of potent antagonists for the human tachykinin NK-2 receptor

A new series of monocyclic pseudopeptide tachykinin NK-2 receptor antagonists has been derived from the lead compound MEN11558. A synthesis for these molecules sharing the same intermediate was designed and performed. The replacement of the succinic moiety with an aspartic acid and the functionalization of its amino group with a wide variety of substituents led to very potent and selective NK-2 antagonists. Best results were obtained through the insertion in position 12 of an amino group with R configuration, linked by a short spacer to a saturated nitrogen heterocycle (morpholine, piperidine, or piperazine). The study led to compounds 54 and 57, endowed with high in vivo potency at very low doses and long duration of action in animal models of bronchoconstriction. In particular 54 and 57 completely inhibited NK-2 agonist induced bronchoconstriction in guinea pig after intratracheal administration at subnanomolar doses (ED50 = 0.27 nmol/kg and 0.15 nmol/kg, respectively).