869096-81-1

Basic information

• Product Name: methyl 3-(4-methoxybenzoyl)-5-nitromethylbenzoate
• Synonyms: methyl 3-(4-methoxybenzoyl)-5-nitromethylbenzoate
• CAS NO: 869096-81-1
• Molecular Weight: 315.282
• Mol File: 869096-81-1.mol

Chemical Properties

• CAS DataBase Reference: methyl 3-(4-methoxybenzoyl)-5-nitromethylbenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 3-(4-methoxybenzoyl)-5-nitromethylbenzoate(869096-81-1)
• EPA Substance Registry System: methyl 3-(4-methoxybenzoyl)-5-nitromethylbenzoate(869096-81-1)

Safety Data

• Hazardous Substances Data: 869096-81-1(Hazardous Substances Data)

Upstream product

• 104-92-7 1-bromo-4-methoxy-benzene 
• 1955-04-0 methyl 5-nitro-3-chloroformylbenzoate 
• 100-66-3 methoxybenzene 
• 1955-46-0 5-nitro-1,3-benzenedicarboxylic acid, monomethyl ester 

Downstream Products

• 869096-88-8 3-(4-methoxybenzyl)-5-nitromethylbenzoic acid 
• 869096-83-3 methyl 3-(4-methoxybenzyl)-5-nitromethylbenzoate 

Relevant articles and documents

Ligands to the (IRAP)/AT4 receptor encompassing a 4-hydroxydiphenylmethane scaffold replacing Tyr2

Analogues of the hexapeptide angiotensin IV (Ang IV, Val1-Tyr2-Ile3-His4-Pro5-Phe6) encompassing a 4-hydroxydiphenylmethane scaffold replacing Tyr2 and a phenylacetic or benzoic acid moiety replacing His4-Pro5-Phe6 have been synthesized and evaluated in biological assays. The analogues inhibited the proteolytic activity of cystinyl aminopeptidase (CAP), frequently referred to as the insulin-regulated aminopeptidase (IRAP), and were found less efficient as inhibitors of aminopeptidase N (AP-N). The best Ang IV mimetics in the series were approximately 20 times less potent than Ang IV as IRAP inhibitors. Furthermore, it was found that the ligands at best exhibited a 140 times lower binding affinity to the membrane-bound IRAP/AT4 receptor than Ang IV. Although the best compounds still exert lower activities than Ang IV, it is notable that these compounds comprise only two amino acid residues and are considerably less peptidic in character than the majority of the Ang IV analogues previously reported as IRAP inhibitors in the literature.

Angiotensin II pseudopeptides containing 1,3,5-trisubstituted benzene scaffolds with high AT2 receptor affinity

Two 1,3,5-trisubstituted aromatic scaffolds intended to serve as γ-turn mimetics have been synthesized and incorporated in five pseudopeptide analogues of angiotensin II (Asp-Arg-Val-Tyr-Ile-His-Pro-Phe), replacing Val-Tyr-Ile, Val-Tyr, or Tyr-Ile. All the tested compounds exhibited nanomolar affinity for the AT2 receptor with the best compound (3) having a Ki of 1.85 nM. Four pseudopeptides were AT2 selective, while one (5) also exhibited good affinity for the AT1 receptor (Ki = 30.3 nM). This pseudopeptide exerted full agonistic activity in an AT2 receptor induced neurite outgrowth assay but displayed no agonistic effect in an AT1 receptor functional assay. Molecular modeling, using the program DISCOtech, showed that the high-affinity ligands could interact similarly with the AT2 receptor as other ligands with high affinity for this receptor. A tentative agonist model is proposed for AT2 receptor activation by angiotensin II analogues. We conclude that the 1,3,5-trisubstituted benzene rings can be conveniently prepared and are suitable as γ-turn mimics.