( Z )-2-(2-aminothiazol-4-yl)-2-acetyloxyiminoacetic acid - CAS 110130-88-6
Category:
Main Product
Product Name:
( Z )-2-(2-aminothiazol-4-yl)-2-acetyloxyiminoacetic acid
Catalog Number:
110130-88-6
Synonyms:
ATAIA; 4-THIAZOLEACETIC ACID, ALPHA-[(ACETYLOXY)IMINO]-2-AMINO-, (Z)-; (Z)-2-(2-AMINOTHIAZOL-4-YL)-2-ACETYLOXYIMINOACETIC ACID; ATAIA:( Z )-2-(2-AMINOTHIAZOL-4-YL)-2-ACETYLOXYIMINOACETIC ACID; ( Z )-2-(2-AMINOTHIAZOL-4-YL)-2-ACETYLOXYIMINOACETIC ACID (ATAIA)
CAS Number:
110130-88-6
Molecular Weight:
229.21
Molecular Formula:
C7H7N3O4S
Quantity:
Data not available, please inquire.
COA:
Inquire
MSDS:
Inquire
Canonical SMILES:
CC(=O)ON=C(C1=CSC(=N1)N)C(=O)O
InChI:
InChI=1S/C7H7N3O4S/c1-3(11)14-10-5(6(12)13)4-2-15-7(8)9-4/h2H,1H3,(H2,8,9)(H,12,13)/b10-5+
InChIKey:
OBRMMFBYPFFKFA-BJMVGYQFSA-N
Chemical Structure
CAS 110130-88-6 ( Z )-2-(2-aminothiazol-4-yl)-2-acetyloxyiminoacetic acid

Reference Reading


1.Synthesis and structure-activity relationships of 7 beta-[(Z)-2-(2- aminothiazol-4-yl)-3-(substituted)-2-propenoylamino]-3-cephems with C-3 substitutions.
Ishikura K1, Kubota T, Minami K, Hamashima Y, Nakashimizu H, Motokawa K, Kimura Y, Miwa H, Yoshida T. J Antibiot (Tokyo). 1994 Apr;47(4):466-76.
Synthesis and biological activity of a series of 7 beta-[(Z)-2-(2- aminothiazol-4-yl)-3-(substituted)-2-propenoylamino]-3-cephe m-4-carboxylic acids with C-3 substitutions and their pivaloyloxymethyl esters are described. These acid compounds exhibited potent antibacterial activity against both Gram-positive and Gram-negative bacteria. Pivaloyloxymethyl esters of selected compounds in this series were found to be well absorbed from small intestine in mice. Pivaloyloxymethyl 7 beta-[(Z)-2-(2-aminothiazol-4-yl)-2-pentenoylamino]-3- carbamoyloxymethyl-3-cephem-4-carboxylase hydrochloride hydrate (S-1108) was finally selected as the candidate for clinical evaluation.
2.Synthesis and structure-activity relationships of 7 beta-[(Z)-2-(2- aminothiazol-4-yl)-3-(substituted)-2-propenoyl-amino]-3- desacetoxymethylcephalosporins.
Ishikura K1, Kubota T, Minami K, Hamashima Y, Nakashimizu H, Motokawa K, Yoshida T. J Antibiot (Tokyo). 1994 Apr;47(4):453-65.
Synthesis and biological activity of a series of 7 beta-[(Z)-2-(2- aminothiazol-4-yl)-3-(substituted)-2-propenoylamino]-3-cephe m-4-carboxylic acids and their pivaloyloxymethyl esters are described. These acid compounds exhibited potent antibacterial activity against both Gram-positive and Gram-negative bacteria. Pivaloyloxymethyl esters of selected compounds in this series were found to be well absorbed from small intestine in mice.
3.A rapid procedure to prepare cefotaxime.
Rodríguez JC1, Hernández R, González M, López MA, Fini A. Farmaco. 2000 May;55(5):393-6.
A rapid procedure is reported for the synthesis of cefotaxime, by acylation of the 7-amino cephalosporanic acid with the 2-mercaptobenzothiazolyl thioester of (Z)-2-[2-aminothiazol-4-yl]-2-methoxyimino acetic acid (MAEM) that is a commercial reagent. The reaction was carried out at room temperature for 1 h, obtaining 95% yield. 2-Mercaptobenzothiazole was recovered as a side-product with a high purity and yield. The proposed method differentiates from those reported previously for a shorter time and very mild reaction condition, as well as for a ready for use reagent.
4.Orally active cephalosporins. II. Synthesis and structure-activity relationships of new 7 beta-[(Z)-2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-cephalospori ns with 1,2,3-triazole in C-3 side chain.
Kume M1, Kubota T, Kimura Y, Nakashimizu H, Motokawa K, Nakano M. J Antibiot (Tokyo). 1993 Jan;46(1):177-92.
The synthesis, antibacterial activity and oral absorbability of 7 beta-[(Z)-2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-3 -(1H-1,2, 3-triazol-4-yl)thiomethylthio-3-cephem-4-carboxylic acid (1g) and related compounds are described. Their oral absorbability was influenced by the spacer length between C-3 of a cephem nucleus and C-4' of 1,2,3-triazole. The SCH2S structure was also found to contribute to their good oral absorption. The quantitative relationship between the bioavailability and the spacer length of cephalosporins (1a-1n) is discussed.