851484-56-5

Basic information

• Product Name: Boc-trans-DL-b-Pro-4-(4-chlorophenyl)-OH
• Synonyms: (3S,4R)-1-Boc-4-(4-chlorophenyl)pyrrolidine-3-carboxylic acid;Boc-(3S,4R)-beta-Pro-4-(4-chlorophenyl)-OH
• CAS NO: 851484-56-5
• Molecular Formula: C₁₆H₂₀ClNO₄
• Molecular Weight: 325.7873
• Mol File: 851484-56-5.mol

Chemical Properties

• Boiling Point: 465.1±45.0 °C(Predicted)
• Appearance: /
• Density: 1.275±0.06 g/cm3(Predicted)
• PKA: 4.27±0.40(Predicted)
• CAS DataBase Reference: Boc-trans-DL-b-Pro-4-(4-chlorophenyl)-OH(CAS DataBase Reference)
• NIST Chemistry Reference: Boc-trans-DL-b-Pro-4-(4-chlorophenyl)-OH(851484-56-5)
• EPA Substance Registry System: Boc-trans-DL-b-Pro-4-(4-chlorophenyl)-OH(851484-56-5)

Safety Data

• Hazardous Substances Data: 851484-56-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Boc-trans-DL-b-Pro-4-(4-chlorophenyl)-OH is used as a key intermediate in the synthesis of pyrrolidinecarboxamide derivatives of piperazines. These derivatives have been identified as potent agonists of the human melanocortin-4 receptor, which plays a crucial role in regulating energy balance and food intake. As a result, they have potential applications in the development of treatments for obesity and related metabolic disorders.
Additionally, Boc-trans-DL-b-Pro-4-(4-chlorophenyl)-OH is utilized in the preparation of substituted 2H-isoquinolin-1-ones. These compounds have demonstrated potent inhibitory activity against Rho-kinase, an enzyme implicated in various pathological conditions, including cardiovascular diseases, fibrosis, and cancer. By targeting Rho-kinase, these inhibitors may offer therapeutic benefits in the treatment of these conditions.

Upstream product

• 851484-55-4 tert-butyl (3S,4R)-3-{[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}-4-(4-chlorophenyl)pyrrolidine-1-carboxylate 
• 862284-39-7 1-tert-butyl 3-methyl (3S,4R)-4-(4-chlorophenyl)pyrrolidine-1,3-dicarboxylate 

Downstream Products

• 851484-57-6 C₃₅H₅₁ClN₄O₄S 
• 862284-42-2 tert-butyl (3R,4S)-3-(4-chlorophenyl)-4-{[(3R,4R,5S)-4-hydroxy-3,5-dimethyl-4-phenylpiperidin-1-yl]carbonyl}pyrrolidine-1-carboxylate 
• 862364-67-8 methyl (3S,4R)-4-(4-chlorophenyl)pyrrolidine-3-carboxylate 
• 1049727-79-8 C₁₁H₁₂ClNO₂*ClH 

Relevant articles and documents

MELANOCORTIN RECEPTOR AGONISTS

The present invention relates to a compound having a good agonistic activity to melanocortin receptor, or pharmaceutically acceptable salt or isomer thereof, and an agonistic composition for melanocortin receptor comprising the same as an active ingredient.

MELANOCORTIN RECEPTOR AGONISTS

The present invention relates to a compound having a good agonistic activity to melanocortin receptor, or pharmaceutically acceptable salt or isomer thereof, and an agonistic composition for melanocortin receptor comprising the same as an active ingredient.

MELANOCORTIN RECEPTOR AGONISTS

The present invention relates to a compound of the following formula 1, pharmaceutically acceptable salt and isomer thereof effective as agonist of melanocortin receptor, and an agonistic composition of melanocortin receptor comprising the same as active ingredient.

Synthesis and characterization of pyrrolidine derivatives as potent agonists of the human melanocortin-4 receptor

A series of trans-4-phenylpyrrolidine-3-carboxamides were synthesized and characterized as potent ligands of the human melanocortin-4 receptor. Interestingly, a pair of diastereoisomers 20f-1 and 20f-2 displayed potent functional agonist and antagonist activity, respectively. Thus, the 3S,4R-compound 20f-1 possessed a Ki of 11 nM and an EC50 of 24 nM, while its 3R,4S-isomer 20f-2 exhibited a Ki of 8.6 and an IC50 of 65 nM. Both compounds were highly selective over other melanocortin receptor subtypes. The MC4R agonist 20f-1 also demonstrated efficacy in diet-induced obese rats.

Pharmaceutically active compounds

The present invention relates to a class of melanocortin MCR4 agonists of general formula (I) wherein R1, R2, R3, R4 and R5 are as defined herein and especially to selective MCR4 agonist compounds, to