108868-95-7

Basic information

• Product Name: andrimid
• Synonyms: andrimid;(βS)-N-[(1S)-2-Methyl-1-[[(3R,4S)-4-methyl-2,5-dioxo-3-pyrrolidinyl]carbonyl]propyl]-β-[[(2E,4E,6E)-1-oxo-2,4,6-octatrienyl]amino]benzenepropanamide
• CAS NO: 108868-95-7
• Molecular Formula: C₂₇H₃₃N₃O₅
• Molecular Weight: 479.58
• Mol File: 108868-95-7.mol

Chemical Properties

• Boiling Point: 795.4°Cat760mmHg
• Flash Point: 234.9°C
• Appearance: /
• Density: 1.155g/cm³
• Vapor Pressure: 2.69E-25mmHg at 25°C
• Refractive Index: 1.552
• PKA: 8.23±0.70(Predicted)
• CAS DataBase Reference: andrimid(CAS DataBase Reference)
• NIST Chemistry Reference: andrimid(108868-95-7)
• EPA Substance Registry System: andrimid(108868-95-7)

Safety Data

• Hazardous Substances Data: 108868-95-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C27H33N3O5/c1-5-6-7-8-12-15-21(31)28-20(19-13-10-9-11-14-19)16-22(32)29-24(17(2)3)25(33)23-18(4)26(34)30-27(23)35/h5-15,17-18,20,23-24H,16H2,1-4H3,(H,28,31)(H,29,32)(H,30,34,35)/b6-5+,8-7+,15-12+/t18-,20+,23+,24+/m1/s1

Upstream product

• 124731-96-0 octatrienyl-D-β-phenylalanine 
• 124731-95-9 (3S)-L-valine-(4S)-methylsuccinimide 
• 792903-64-1 (3S)-β-phenylalanine-L-valine-(4S)-methylsuccinimide 
• 97329-94-7 (2E,4E,6E)-octa-2,4,6-trienoic acid 
• 2174-58-5 L-malic acid 
• 124731-94-8 (3S)-Boc-L-valine-(4S)-methylsuccinimide 
• 214679-37-5 (S)-3-((2E,4E,6E)-Octa-2,4,6-trienoylamino)-3-phenyl-propionic acid tert-butyl ester 
• 37088-66-7 (3S)-methyl 3-amino-3-phenylpropanoate 
• 142-83-6 trans,trans-2,4-Hexadienal 
• 5941-49-1 2E,4E,6E-octatrienoic acid ethyl ester 
• 137271-80-8 [(S)-2-Methyl-1-((3R,4S)-4-methyl-2,5-dioxo-pyrrolidine-3-carbonyl)-propyl]-carbamic acid benzyl ester 
• 14898-52-3 D-β-phenylalanine methyl ester 
• 124817-98-7 (2S,3R,5S)-5-tert-Butoxycarbonylamino-3-carbamoyl-2,6-dimethyl-4-oxo-heptanoic acid benzyl ester 
• 124731-92-6 ((S)-3-Carbamoyl-1-isopropyl-2-oxo-propyl)-carbamic acid tert-butyl ester 

Relevant articles and documents

Pyrrolidinedione derivatives as antibacterial agents with a novel mode of action

The pseudopeptide pyrrolidinedione natural products moiramide B and andrimid represent a new class of antibiotics that target bacterial fatty acid biosynthesis. Structure-activity relationship (SAR) studies revealed a high degree of variability for the fa

Asymmetric syntheses of moiramide B and andrimid

The first highly diastereoselective asymmetric syntheses of moiramide B 2 and andrimid 3 have been achieved using lithium amide (R)-6 and pyrrolidinone auxiliary (R)-9. Pyrrolidinone auxiliary (R)-9 was used to create the novel (S)-3-methyl-N-benzyloxysuc

A convenient diastereoselective total synthesis of andrimid

A convenient diastereoselective synthesis of andrimid was accomplished in a straightforward approach and also several β-substituted cyclic imides were prepared in a facile manner.

Stereocontrolled Synthesis of Andrimid and a Structural Requirement for the Activity

Total synthesis of an antibiotic Andrimid was accomplished stereospecifically: it was shown that the chiralities at C-3 and C-4 should be R and S, respectively, and the presence of the (4S)-methyl group is important for the activity.