151867-81-1

Usage

Uses

Used in Pharmaceutical Industry:
DMP 323 is used as a pharmaceutical compound for its potential therapeutic properties. The specific application reason is not provided in the materials, but the unique structure of DMP 323 suggests that it may have interactions with biopolymers and macromolecules, making it a promising candidate for drug development.
Used in Chemical Synthesis:
DMP 323 can be used as a key intermediate in the synthesis of various complex organic compounds. Its unique structure with multiple functional groups allows for further chemical modifications and the creation of new molecules with specific properties and applications.
Used in Research and Development:
DMP 323 may be utilized in research and development settings to study its chemical properties, reactivity, and potential interactions with other molecules. This can lead to a better understanding of its applications and the development of new compounds with improved properties.

InChI:InChI=1/C35H38N2O5/c38-23-29-15-11-27(12-16-29)21-36-31(19-25-7-3-1-4-8-25)33(40)34(41)32(20-26-9-5-2-6-10-26)37(35(36)42)22-28-13-17-30(24-39)18-14-28/h1-18,31-34,38-41H,19-24H2/t31-,32-,33+,34+/m1/s1

Upstream product

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• 41518-17-6 C₂₂H₂₅NO₆ 
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• 153181-25-0 (4R,5S,6S,7R)-hexahydro-5,6-bis(2-methoxyethoxymethoxy)-4,7-bis(phenylmethyl)-2H-1,3-diazepin-2-one 
• 1053243-89-2 C₄₃H₄₈N₄O₇ 
• 183814-19-9 ((1S,2R,3S,4R)-1-Benzyl-4-benzyloxycarbonylamino-2,3-dihydroxy-5-phenyl-pentyl)-carbamic acid benzyl ester 
• 63219-70-5 N-(benzyloxycarbonyl)-D-phenylalaninal 
• 58917-85-4 N-(benzyloxycarbonyl)-D-phenylalaninol 

Relevant academic research and scientific papers

Cyclic HIV protease inhibitors: Synthesis, conformational analysis, P2/P2' structure-activity relationship, and molecular recognition of cyclic ureas

High-resolution X-ray structures of the complexes of HIV-1 protease (HIV-1PR) with peptidomimetic inhibitors reveal the presence of a structural water molecule which is hydrogen bonded to both the mobile flaps of the enzyme and the two carbonyls flanking

Preparation and structure-activity relationship of novel P1/P1'- substituted cyclic urea-based human immunodeficiency virus type-1 protease inhibitors

A series of novel P1/P1'-substituted cyclic urea-based HIV-1 protease inhibitors was prepared. Three different synthetic schemes were used to assemble these compounds. The first approach uses amino acid-based starting materials and was originally used to prepare DMP 323. The other two approaches use L-tartaric acid or L-mannitol as the starting material. The required four contiguous R,S,S,R centers of the cyclic urea scaffold are introduced using substrate control methodology. Each approach has specific advantages based on the desired P1/P1' substituent. Designing analogs based on the enzyme's natural substrates provided compounds with reduced activity. Attempts at exploiting hydrogen bond sites in the S1/S1' pocket, suggested by molecular modeling studies, were not fruitful. Several analogs had better binding affinity compared to our initial leads. Modulating the compound's physical properties led to a 10-fold improvement in translation resulting in better overall antiviral activity.

Stereoselective synthesis of HIV-1 protease inhibitor, DMP 323

DMP 323, a potent HIV-1 protease inhibitor, has been synthesized by an efficient stereoselective process, amenable to large scale preparations. The core C2 symmetric diol was synthesized by a stereoselective pinacol coupling of CBZ protected D-phenylalanine. Judicious selection of protecting groups allowed cyclic urea formation under mild conditions, enhanced the ease of bis-alkylation, and led te intermediates which were easily purified without chromatography. Additionally, a one-pot, high yield process was developed te prepare the alkylating agent, 4-[(triphenylmethoxy)methyl]benzyl chloride from 1,4-benzenedimethanol.