4-Thia-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid, 6-(1-hydroxyethyl)-7-oxo-, [5R-[5α,6α(R*)]]-

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4-Thia-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid, 6-(1-hydroxyethyl)-7-oxo-, [5R-[5α,6α(R*)]]-
Category Others
Catalog number BBF-05648
CAS 91685-69-7
Molecular Weight 215.23
Molecular Formula C8H9NO4S

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Specification

Synonyms (5R,6R)-6-((R)-1-hydroxyethyl)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid; (5R-(5alpha,6alpha(R*)))-6-(1-Hydroxyethyl)-7-oxo-4-thia-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid; 6-(1-Hydroxyethyl)-7-oxo-4-thia-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid, (5R-(5alpha,6alpha(R*)))-
IUPAC Name (5R,6R)-6-[(1R)-1-hydroxyethyl]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
Canonical SMILES CC(C1C2N(C1=O)C(=CS2)C(=O)O)O
InChI InChI=1S/C8H9NO4S/c1-3(10)5-6(11)9-4(8(12)13)2-14-7(5)9/h2-3,5,7,10H,1H3,(H,12,13)/t3-,5-,7-/m1/s1
InChI Key IYPZTSDEYRDCBO-HGWBJXFBSA-N

Properties

Boiling Point 514.0±50.0°C at 760 mmHg
Density 1.67±0.1 g/cm3

Reference Reading

1. Comparative stability of carbapenem and penem antibiotics to renal dehydropeptidase-I
M Hikida, M Yoshida, S Mitsuhashi Arzneimittelforschung. 1993 Jan;43(1):71-3.
Comparison has been made on the stability of 4 carbapenems and 3 penems against porcine renal dehydropeptidase-I (DHP-I). Evaluated were the carbapenems (5R,6S)-3-[[2-(formimidoylamino)ethyl]thio]-6-[(R)-1-hydroxyethyl] - 7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid monohydrate, CAS 74431-23-5, in the following called FAC, (5R,6S)-3-[(S)-1-(acetimidoylpyrrolidin-3-yl)thio]-6-[(R)-1- hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0] hept-2-ene-2-carboxylic acid, CAS 87726-17-8, in the following called AHC, (4R,5S,6S)-3-[[(3S,5S)-5-dimethylcarbamoylpyrrolidin-3-yl]thio]-6- [(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2- carboxylic acid trihydrate, CAS 96036-03-2, in the following called DHC. (1R,5S,6S)-2-[(6,7-dihydro-5H-pyrazolo[1,2-a] [1,2,4]triazolium-6-yl)thio]-6-[(R)-1-hydroxyethyl]-1-methyl-ca rbapen - 2-em-3-carboxylate, in the following called DHM, and the penems (5R,6S)-6-[(R)-1-hydroxyethyl]-7-oxo-3-[(R)-2-tetrahydrofuryl]-4-thia-1 - azabicyclo [3.2.0]hept-2-ene-2-carboxylic acid sodium salt, in the following called HTC, (5R,6S)-2-carbamoyloxymethyl-6-[(1R)-hydroxyethyl]-2-penem-3-carboxylic acid, in the following called CHC, (5R,6S)-6-[(R)-1-hydroxyethyl]-3-[(3S)-(cis-1-oxotetrahydrothiophen++ +-3-yl) thio]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, in the following called HHC. According to the comparison of the Vmax/Km ratios, the order of stability of the compounds to hydrolysis by renal DHP-I was as follows: DHM >> DHC > HHC > AHC > HTC > CHC > FAC. From this result it is particularly noteworthy that DHM has extremely high stability against renal DHP-I.

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