89226-13-1

Basic information

• Product Name: TERT-BUTYL 2-AMINO-2-THIOXOETHYLCARBAMATE
• Synonyms: TERT-BUTYL 2-AMINO-2-THIOXOETHYLCARBAMATE;TERT-BUTYL THIOCARBAMOYLMETHYLCARBAMATE;Carbamic acid, (2-amino-2-thioxoethyl)-, 1,1-dimethylethyl ester (9CI);tert-Butyl N-(carbamothioylmethyl)carbamate;Thiocarbamoylmethyl-carbamic acid tert-butyl ester
• CAS NO: 89226-13-1
• Molecular Formula: C₇H₁₄N₂O₂S
• Molecular Weight: 190.26326
• Product Categories: N-BOC
• Mol File: 89226-13-1.mol
• Article Data: 1

Chemical Properties

• Melting Point: 129 °C
• Appearance: /
• Density: 1.152g/cm³
• Refractive Index: 1.525
• Storage Temp.: 2-8°C
• PKA: 11.35±0.46(Predicted)
• CAS DataBase Reference: TERT-BUTYL 2-AMINO-2-THIOXOETHYLCARBAMATE(CAS DataBase Reference)
• NIST Chemistry Reference: TERT-BUTYL 2-AMINO-2-THIOXOETHYLCARBAMATE(89226-13-1)
• EPA Substance Registry System: TERT-BUTYL 2-AMINO-2-THIOXOETHYLCARBAMATE(89226-13-1)

Safety Data

• RIDADR: 2811
• Hazardous Substances Data: 89226-13-1(Hazardous Substances Data)

Usage

Uses

tert-?Butyl 2-?Amino-?2-?thioxoethylcarbamate is a reactant used in the synthesis of polyazole peptide antibiotic Goadsporin which is a powerful antibiotic. Also used in the total synthesis of ME1036 which is a broad spectrum parenteral carbapenem.

Synthesis Reference(s)

The Journal of Organic Chemistry, 50, p. 2787, 1985 DOI: 10.1021/jo00215a040

InChI:InChI=1/C7H14N2O2S/c1-7(2,3)11-6(10)9-4-5(8)12/h4H2,1-3H3,(H2,8,12)(H,9,10)

Upstream product

• 31954-27-5 N-(tert-butoxycarbonyl)glycine methyl ester 

Downstream Products

• 1043577-34-9 (S,E)-2-(trimethylsilyl)ethyl 3-(((S)-2-((R)-2'-(((tert-butoxycarbonyl)amino)methyl)-4-methyl-4,5-dihydro[2,4'-bithiazole]-4-carboxamido)-3-methylbutanoyl)oxy)-7-(tritylthio)hept-4-enoate 
• 1315334-32-7 (S,E)-2-(trimethylsilyl)ethyl 3-(2-((R)-2-(2-((tert-butoxycarbonylamino)methyl)thiazol-4-yl)-4-methyl-4,5-dihydrothiazole-4-carboxamido)acetoxy)-7-(tritylthio)hept-4-enoate 
• 1315334-33-8 (S,E)-2-(trimethylsilyl)ethyl 3-(3-((R)-2-(2-((tert-butoxycarbonylamino)methyl)thiazol-4-yl)-4-methyl-4,5-dihydrothiazole-4-carboxamido)propanoyloxy)-7-(tritylthio)hept-4-enoate 
• 1315334-38-3 (S,E)-2-(trimethylsilyl)ethyl 3-((S)-2-(2-(2-((tert-butoxycarbonylamino)methyl)thiazole-4-carboxamido)-2-methylpropanamido)-3-methylbutanoyloxy)-7-(tritylthio)hept-4-enoate 
• 89226-27-7 Glycin-thioamid-hyrochlorid 
• 871715-97-8 tert-butyl N-[(4-benzylthiazol-2-yl)methyl]carbamate 
• 1415580-95-8 (S,E)-2-(trimethylsilyl)ethyl 3-(((S)-2-(2-(5-(2-(((tert-butoxycarbonyl)amino)methyl)thiazol-4-yl)-2H-tetrazol-2-yl)acetamido)-3-methylbutanoyl)oxy)-7-(tritylthio)hept-4-enoate 

Relevant articles and documents

RITA Mimics: Synthesis and Mechanistic Evaluation of Asymmetric Linked Trithiazoles

The established cytotoxic agent RITA contains a thiophene-furan-thiophene backbone and two terminal alcohol groups. Herein we investigate the effect of using thiazoles as the backbone in RITA-like molecules and modifying the terminal groups of these trithiazoles, thereby generating 41 unique structures. Incorporating side chains with varied steric bulk allowed us to investigate how size and a stereocenter impacted biological activity. Subjecting compounds to growth inhibition assays on HCT-116 cells showed that the most potent compounds 7d, 7e, and 7h had GI50 values of 4.4, 4.4, and 3.4 μM, respectively, versus RITA (GI50 of 800 nM). Analysis of these compounds in apoptosis assays proved that 7d, 7e, and 7h were as effective as RITA at inducing apoptosis. Evaluating the impact of 7h on proteins targeted by RITA (p53, c-Myc, and Mcl-1) indicated that it acts via a different mechanism of action to that of RITA. RITA suppressed Mcl-1 protein via p53, whereas compound 7h suppressed Mcl-1 expression via an alternative mechanism independent of p53.