123411-96-1

Basic information

• Product Name: Cyclopentanecarboxylic acid, 3,4-dihydroxy-, methyl ester, (1alpha,3beta,4beta)- (9CI)
• Synonyms: Cyclopentanecarboxylic acid, 3,4-dihydroxy-, methyl ester, (1alpha,3beta,4beta)- (9CI)
• CAS NO: 123411-96-1
• Molecular Formula: C₇H₁₂O₄
• Molecular Weight: 160.16778
• Product Categories: CARBOXYLICESTER;CYCLOPENTANE
• Mol File: 123411-96-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Cyclopentanecarboxylic acid, 3,4-dihydroxy-, methyl ester, (1alpha,3beta,4beta)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclopentanecarboxylic acid, 3,4-dihydroxy-, methyl ester, (1alpha,3beta,4beta)- (9CI)(123411-96-1)
• EPA Substance Registry System: Cyclopentanecarboxylic acid, 3,4-dihydroxy-, methyl ester, (1alpha,3beta,4beta)- (9CI)(123411-96-1)

Safety Data

• Hazardous Substances Data: 123411-96-1(Hazardous Substances Data)

Upstream product

• 58101-60-3 methyl cyclopent-3-ene-1-carboxylate 
• 123411-96-1 (1rs,3R,4S)-3,4-dihydroxycyclopentanecarboxylic acid methyl ester 

Downstream Products

• 123411-96-1 methyl (1SR,3RS,4SR)-3,4-dihydroxycyclopentanecarboxylate 
• 1207637-99-7 methyl (1RS,3RS,4SR)-3,4-dihydroxycyclopentanecarboxylate 

Relevant articles and documents

Diastereoselective synthesis of conformationally restricted KOR agonists

In order to analyze the bioactive conformation of flexible KOR agonists the ethylenediamine KOR pharmacophore was conformationally constrained by incorporation into a bicyclic system. For this purpose, 2-azabicyclo[3.2.1.]octan-7-amines were designed, synthesized and pharmacologically evaluated. The primary amine 14 as first key intermediate was prepared in a six-step synthesis starting with methyl cyclopent-3-enecarboxylate 9. Whereas phenylacetamides failed to provide bicyclic compounds, the intramolecular nucleophilic substitution of the sulfonamide 25 was initiated by deprotonation with NaH affording the bicyclic compound 26 in 72% yield. The three-step introduction of the pharmacophoric pyrrolidine ring started with nucleophilic substitution of exo-configured tosylate 26 with NaN3, which unexpectedly occurred under retention of configuration leading to exo-configured azide 31. The final KOR agonists 35 and 36 with exo-configured amino moieties were obtained by removal of the N-tosyl moiety of 33 and introduction of the second pharmacophoric element by acylation with dihalophenylacetyl chlorides. The KOR affinity of the pyrrolidine 35a is in the high nanomolar range (Ki = 862 nM). The low KOR affinity is explained by a non-appropriate dihedral angle of 137°/141° of the N(pyrrolidine)-C-C-N(acyl) system. As observed for stereoisomers of potent KOR agonists, phenylacetamide 35a and more importantly sulfonamides 33a and 33b show moderate affinity at σ1 receptors (Ki = 109-208 nM). This journal is

ANTIMICROBIAL AGENTS

The invention provides novel analogues of enacyloxin Ha and their pharmaceutically acceptable salts, metabolites, isomers (e.g. stereoisomers) and prodrugs. Such compounds are effective in the treatment of infections caused by Gram-negative bacteria such as Acinetobacter baumannii. Compounds in accordance with the invention include those of formula (A), and their pharmaceutically acceptable salts, metabolites, isomers (e.g. stereoisomers) and prodrugs: In formula (A): X is 0 or NRx (where R* is either H or C1-3 alkyl, e.g. CH3); R1 is a 5- or 6-membered, saturated or unsaturated, carbocyclic ring optionally substituted by one or more substituents, or R1 is an optionally substituted straight-chained or branched C-1-6 alkyl group (e.g. C1-3 alkyl group); R2 is H, F, CI, Br, I or CH3; R3 is H or OH; R8 is a straight-chained or branched C1-8 alkyl group (e.g. a C1-6 aikyl group); Y is one of the following groups: (wherein each * denotes the point of attachment of the group to the remainder of the molecule; R9 is H, F, CI, Br or I; R4 and R5 are independently selected from H and OH, or R4 and R5 together are =0, preferably R4 is H and R5 is OH; R6 is H, F, CI, Br, I or CH3; R7 is H and R7' is OH, or R7 and R7' together are =0, preferably R7 is H and R7' is OH); and each— independently represents an optional bond (i.e. each of C2-C3, C4-C5, C6-C7, C8-C9 and C10-C11 are independently either C-C (single) or C=C (double) bonds).

ANTIBACTERIAL BIAROMATIC DERIVATIVES

The invention relates to antibacterial compounds of formula I (I) wherein R is H, cyano, alkoxy, cyanomethoxy, cycloalkylmethoxy, hydroxyalkoxy, alkoxyalkoxy, alkoxycarbonyl, 2-ethoxy-2-oxoethoxy, 2-(methylamino)-2-oxoethoxy, (l-cyanocyclobutyl)methoxy, 3-hydroxy-pyrrolidin-l-yl or 3,4-dihydroxycyclopentyl)methoxy; U1 is N or CR1, U2 is N or CR2, U3 is N or CR3 and U4 is N or CR4, it being understood that at most three of U1, U2, U3 and U4 can be N at the same time; V1 is N or CR5, V2 is N or CR6, V3 is N or CR7 and V4 is N or CH, it being understood that at most two of V1, V2, V3 and V4 can be N at the same time; R1 is H, cyano, hydroxy or alkoxy; R2 is H, hydroxy or alkoxy; R3 is H, cyano, hydroxy, alkoxy or carboxamido; R4 is H or alkoxy; R5 is H, hydroxy or halogen; R6 is H, hydroxy or halogen; R7 is H; the dotted line "_____ " represents a bond or is absent; W represents CH or N when the dotted line "_____ " is a bond, or W represents CH2 when the dotted line "_____ " is absent; X represents CH or N; and Q represents O or S; and salts thereof.

ANTIBACTERIAL AGENTS

Antibacterial compounds of formula (I) are provided, as well as stereoisomers and pharmaceutically acceptable salts thereof; pharmaceutical compositions comprising such compounds; methods of treating bacterial infections by the administration of such compounds; and processes for the preparation of such compounds.

NITROOXY CYCLOALKANE DERIVATIVES

A compound having the structure wherein Y is selected from the group consisting of –C(O)OR2, -C(O)NHR8, -C(CH2)1-2OR3, OH, and or a pharmaceutically acceptable salt thereof, and methods of using the compounds for treating hypertension.