27958-06-1

Basic information

• Product Name: DEACETYLANISOMYCIN FROM STREPTOMYCES*GRISEOLUS
• Synonyms: DEACETYLANISOMYCIN FROM STREPTOMYCES*GRISEOLUS;deacetylanisomycin;SA 3097D1
• CAS NO: 27958-06-1
• Molecular Formula: C₁₂H₁₇NO₃
• Molecular Weight: 223.27
• Mol File: 27958-06-1.mol
• Article Data: 13

Chemical Properties

• Melting Point: 176-179°
• Boiling Point: 390.693°C at 760 mmHg
• Flash Point: 190.084°C
• Appearance: /
• Density: 1.233g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.587
• Storage Temp.: 2-8°C
• PKA: 9.2(at 25℃)
• CAS DataBase Reference: DEACETYLANISOMYCIN FROM STREPTOMYCES*GRISEOLUS(CAS DataBase Reference)
• NIST Chemistry Reference: DEACETYLANISOMYCIN FROM STREPTOMYCES*GRISEOLUS(27958-06-1)
• EPA Substance Registry System: DEACETYLANISOMYCIN FROM STREPTOMYCES*GRISEOLUS(27958-06-1)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 27958-06-1(Hazardous Substances Data)

Usage

Description

Deacetylanisomycin, derived from Streptomyces griseolus, is a dihydroxypyrrolidine with antimalarial and anticancer properties. It is a potent inhibitor of protein synthesis and has shown cytotoxic effects on certain cancer cell lines. Although considered inactive, it acts as a potent growth regulator in plants, and its pharmacological properties are not well-researched.

Uses

Used in Pharmaceutical Industry:
Deacetylanisomycin is used as an antimalarial agent, inhibiting the growth of P. falciparum strains K1 and T9-96 in vitro. It also exhibits cytotoxicity against LU99 lung carcinoma and MCF-7 breast cancer cells, making it a potential candidate for anticancer drug development.
Used in Agricultural Industry:
Deacetylanisomycin serves as an agricultural fungicide, leveraging its potent inhibitory effects on protein synthesis to control fungal growth and protect crops.
Used in Research Applications:
Deacetylanisomycin is utilized as a negative control for assessing protein synthesis inhibitor activity in molluscan neurons, providing a benchmark for evaluating the effectiveness of other potential inhibitors in biological research.

InChI:InChI=1/C12H17NO3/c1-16-9-4-2-8(3-5-9)6-10-12(15)11(14)7-13-10/h2-5,10-15H,6-7H2,1H3/t10-,11+,12+/m0/s1

Upstream product

• 115828-77-8 (2R,3S,4S)-3,4-bis(benzyloxy)-2-(4-methoxybenzyl)-pyrrolidine 
• 100449-58-9 (2R,3S,4S)-2-(4-methoxybenzyl)-3,4-O-bis-(methoxymethyl)pyrrolidine 
• 112463-98-6 Acetic acid (3R,4S,5R)-4-hydroxy-5-(4-methoxy-benzyl)-2-oxo-pyrrolidin-3-yl ester 
• 23006-20-4 (3R,4S,5R)-N-Benzyl-3,4-dihydroxy-5-p-anisyl-pyrrolidon-2 
• 228396-56-3 {(1R)-1-(N-tert-butoxycarbonylamino)-1-deoxy-1-(p-methoxybenzyl)-2,3-O-isopropylidene-4-chloro-L-threitol} 
• 165877-97-4 (2R,3S,4S)-N-benzyl-3,4-dihydroxy-2-(4-methoxybenzyl)pyrrolidine 
• 228396-51-8 {(1R)-1-(N-benzyl-N-hydroxyamino)-1-deoxy-1-(p-methoxybenzyl)-4-O-benzyl-2,3-O-isopropylidene-L-threitol} 
• 293314-35-9 (2S,3S,4R)-4-(benzylamino)-2,3-O-isopropylidene-5-(4-methoxyphenyl)pentane-1,2,3-triol 
• 606147-97-1 (2S,3S,4R)-1-O-benzyl-4-(benzylamino)-2,3-O-isopropylidene-5-(4-methoxyphenyl)pentane-1,2,3-triol 
• 94790-24-6 (2R)-tert-butoxycarbonylamino-3-(4-methoxyphenyl)propionic acid methyl ester 
• 139183-60-1 [(R)-1-Formyl-2-(4-methoxy-phenyl)-ethyl]-carbamic acid tert-butyl ester 
• 120349-75-9 (2R)-2-(tert-butoxycarbonyl)amino-3-(4-methoxyphenyl)propan-1-ol 
• 228396-55-2 (1R,4S,5R)-5-[1-(tert-butoxycarbonyl)amino-2-(4-methoxyphenyl)ethyl]-2,2-dimethyl-1,3-dioxolan-4-ylmethanol 
• 478623-17-5 ethyl (2E,4R)-4-(tert-butoxycarbonyl)amino-5-(4-methoxyphenyl)pent-2-enoate 

Downstream Products

• 27958-05-0 (2R,3S,4S)-N-(benzyloxycarbonyl)-3,4-dihydroxy-2-(4-methoxybenzyl)pyrrolidine 
• 111765-92-5 (2S,3R,4R)-N-(benzyloxycarbonyl)-3,4-dihydroxy-2-(4-methoxybenzyl)pyrrolidine 
• 82916-86-7 N-((benzyloxy)carbonyl)-3β,4α-dihydroxy-2β-(p-methoxybenzyl)pyrrolidine 
• 21497-40-5 (+/-)-anisomycin 
• 111602-18-7 (2S,3R,4R)-3-Acetoxy-2-(4-methoxy-benzyl)-4-(2,2,2-trichloro-ethoxycarbonyloxy)-pyrrolidine-1-carboxylic acid benzyl ester 

Relevant articles and documents

A common strategy towards the synthesis of 1,4-dideoxy-1,4-imino-L-xylitol, deacetyl (+)-anisomycin and amino-substituted piperidine iminosugars

A strategy towards the synthesis of three different target molecules, namely 1,4-dideoxy-1,4-imino-L-xylitol, deacetyl (+)-anisomycin and amino-substituted piperidine iminosugars, molecules of potential biological and medicinal significance, is reported from a common amino-vicinal diol intermediate derived from tri-O-benzyl-D-glucal. Construction of the key pyrrolidine ring present in 1,4-dideoxy-1,4-imino-L-xylitol and (+)-anisomycin was a consequence of thermodynamically driven concomitant intramolecular nucleophilic addition reaction of the amino group to the resultant aldehyde obtained by oxidative cleavage of the amino-vicinal diol. Alternatively, double nucleophilic substitution on an amino-diol, after mesylation, with various amines delivered amino-substituted piperidine iminosugars in good yields.

A new approach to (+)-anisomycin

An efficient approach to enantiomerically pure (+)-deacetylanisomycin 2a and a formal synthesis of (+)-anisomycin 2 (11% overall yield in 10 steps) have been achieved through simple and good yielding reactions, starting from 1,2:3,4:5,6-tri-O-isopropylidene-D-mannitol 3. Grignard reaction and intramolecular cyclisation reactions are key steps in the strategy.

Highly diastereoselective additions to polyhydroxylated pyrrolidine cyclic imines: Ready elaboration of aza-sugar scaffolds to create diverse carbohydrate-processing enzyme probes

Representative diastereomeric, erythritol and threitol polyhydroxylated pyrrolidine imine scaffolds have been rapidly elaborated to diversely functionalized aza-sugars through highly diastereoselective organometallic (RM) additions (R = Me, Et, allyl, hex