39544-74-6

Basic information

• Product Name: BENZOTRIPT
• Synonyms: benzotripte;(S)-α-(4-Chlorobenzoylamino)-1H-indole-3-propionic acid;Nα-(4-Chlorobenzoyl)-L-tryptophan
• CAS NO: 39544-74-6
• Molecular Formula: C18H15ClN2O3
• Molecular Weight: 342.78
• EINECS: 254-500-0
• Mol File: 39544-74-6.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 643.7°C at 760 mmHg
• Flash Point: 343.1°C
• Appearance: /
• Vapor Pressure: 1.88E-17mmHg at 25°C
• Storage Temp.: -20°C
• Solubility: Soluble in DMSO (up to at least 25 mg/ml)
• Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
• CAS DataBase Reference: BENZOTRIPT(CAS DataBase Reference)
• NIST Chemistry Reference: BENZOTRIPT(39544-74-6)
• EPA Substance Registry System: BENZOTRIPT(39544-74-6)

Safety Data

• Hazardous Substances Data: 39544-74-6(Hazardous Substances Data)

Usage

Description

BENZOTRIPT, with the chemical formula C12H15N, is a pharmaceutical compound that primarily functions as an antagonist for the cholecystokinin receptor. It is known to interfere with the interaction between cholecystokinin and related peptides, thereby playing a role in the regulation of various physiological processes. Additionally, BENZOTRIPT has been reported to enhance the analgesic effects of morphine through its interaction with opioid receptors.

Uses

Used in Pharmaceutical Industry:
BENZOTRIPT is used as a receptor antagonist for the treatment of conditions related to the cholecystokinin receptor. Its application reason is to modulate the interaction between cholecystokinin and its receptor, potentially leading to therapeutic benefits in various conditions.
BENZOTRIPT is also used as an analgesic enhancer in combination with morphine for the management of pain. The application reason is its ability to potentiate the effects of morphine by interacting with opioid receptors, which can result in improved pain relief and potentially reduced morphine dosage requirements.

References

1) Hahne (1981), Proglumide and benzotript: Members of a different class of cholecystokinin receptor antagonists; Proc. Natl. Acad. Sci. USA. 78 6304 2) Gaudreau et al. (1990), Cholecystokinin antagonists proglumide, lorglumide and benzotript, but not L-364,718, interact with brain opioid binding sites; Neuropeptides 16 51

InChI:InChI=1/C18H15ClN2O3/c19-13-7-5-11(6-8-13)17(22)21-16(18(23)24)9-12-10-20-15-4-2-1-3-14(12)15/h1-8,10,16,20H,9H2,(H,21,22)(H,23,24)/p-1/t16-/m1/s1

Upstream product

• 122-01-0 4-chloro-benzoyl chloride 
• 73-22-3 L-Tryptophan 
• 74-11-3 para-chlorobenzoic acid 

Downstream Products

• 1435265-14-7 N-(N-4-chlorobenzoyl-L-tryptophanyl)-D-phenylalanine methyl ester 
• 95579-05-8 (S)-2-(4-Chloro-benzoylamino)-3-(2-oxo-2,3-dihydro-1H-indol-3-yl)-propionic acid 

Relevant articles and documents

Mercaptoacetate thioesters and their hydrolysate mercaptoacetic acids jointly inhibit metallo-β-lactamase L1

The 'superbug' infection caused by metallo-β-lactamases (MβLs) including L1 has grown into an emerging threat. To probe whether mercaptoacetate thioesters inhibiting L1 is a contribution of the thioester itself or its hydrolysate, ten mercaptoacetate thioesters 1-10 were synthesized, which specifically inhibited L1, exhibiting IC50 values ranging from 0.17 to 1.2 μM, and 8 was found to be the best inhibitor (IC50 = 0.17 μM). These thioesters restored the antimicrobial activity of cefazolin against E. coli expressing L1 by 2-4-fold. UV-vis monitoring showed that 1, 8 and 9 were unhydrolyzed in Tris buffer (pH 6.0-8.5), but hydrolyzed by L1; further HPLC monitoring indicated that 1/3 of the thioester 9 was converted to mercaptoacetic acid. STD-NMR monitoring suggested that both the thioester and its hydrolysate mercaptoacetic acid jointly inhibited L1.

N-Benzoyl amino acids as ICAM/LFA-1 inhibitors. Part 2: Structure-activity relationship of the benzoyl moiety

o-Bromobenzoyl L-tryptophan 1 inhibits the association of LFA-1 with ICAM-1 with an IC50 of 1.7μM. Evaluation of the structure-activity relationship of the benzoyl moiety shows that 2,6-di-substitutions greatly enhance potency of this class of inhibitors. Electronegative substitutions that favor a 90°angle between the benzoyl ring and the amide bond yield the most potent compounds. There is a strong correlation between the potency of the compounds and the difference between the ab initio energy at 90°and the global minima energy for given compounds. Combining the favored benzoyl substitutions with L-histidine and L-asparagine resulted in a 15-fold increase in potency over compound 1.

N-p-chlorobenzoyl tryptophane, salts and compositions thereof

Pharmaceutically active L-tryptophane compounds comprising the compound of the formula: STR1 AND ITS CALCIUM, MAGNESIUM AND ALUMINUM SALTS. These compounds exhibit superior pharmacologic activity on the gastroenteric tract.