5335-05-7Relevant articles and documents
Evaluation of the antibacterial efficacy of diesters of azelaic acid
Charnock, Colin,Brudeli, Bjarne,Klaveness, Jo
, p. 589 - 596 (2004)
A number of diesters of the topical dermatosis treatment azelaic (nonanedioic) acid were prepared and tested for antibacterial effect. Two esters, bis-[(hexanoyloxy)methyl] nonanedioate and especially bis-[(butanoyloxy)methyl] nonanedioate showed promising activity against acne related bacteria in vitro. No activity of azelaic acid was detected in Mueller Hinton II agar at pH 7.3 when using the agar diffusion method, whereas both esters gave zones of growth inhibition. At pH 5.6, activity of azelaic acid was detected. At this pH, the zones of inhibition and MIC values obtained with azelaic acid were smaller than those of bis-[(butanoyloxy)methyl] nonanedioate for all test organisms. A preparation for topical use containing 20% (w/w) bis-[(butanoyloxy)methyl] nonanedioate, and the commercially available Skinoren (20% (w/w) azelaic acid), were compared for antibacterial effect against cutaneous bacteria using contact plate analyses of the skin. Though Skinoren was usually most effective, the differences were not statistically significant. Furthermore, bacteria surviving contact with the topical preparations were invariably more sensitive to the ester than to azelaic acid upon subculturing onto agar (pH 5.6) containing either preparation at 0.2-0.7mg/ml. This might indicate that other factors, such as the composition of the cream base, mitigate the antibacterial activity of the ester. It is proposed that the pharmacological and microbiological properties of bis-[(butanoyloxy)methyl] nonanedioate are worthy of further study based on an extended screening of acne sufferers.
Synthesis and antimicrobial activity of the hybrid molecules between amoxicillin and derivatives of benzoic acid
Li, Zhonglin,Lin, Hao,Zhou, Junwen,Chen, Liangzhu,Pan, Zhikun,Fang, Binghu
, p. 198 - 206 (2020/09/23)
Due to the increasing problem of bacterial resistance worldwide, the demand for new antibiotics is becoming increasingly urgent. We wished to: (a) prepare hybrid molecules by linking different pharmacophores by chemical bonds; (b) investigate the antib acterial activity of these hybrids using drug-sensitive and drug-resistant pathogens in vitro and vivo. A series of hybrid molecules with a diester structure were designed and synthesized that linked amoxicillin and derivatives of benzoic acid via a methylene bridge. Synthesized compounds were evaluated for activities against Gram-positive bacteria (Staphylococcus aureus American Type Culture Collection [ATCC] 29213, ATCC 11632; methicillin-resistant S. aureus [MRSA] 11; Escherichia coli ATCC 25922) and Gram-negative bacteria (Salmonella LS677, GD836, GD828, GD3625) by microdilution of broth. Synthesized compounds showed good activity against Gram-positive and Gram-negative bacteria in vitro. In particular, amoxicillin-p-nitrobenzoic acid (6d) showed good activity against Salmonella species and had better activity against methicillin-resistant S. aureus (minimum inhibitory concentration [MIC] = 64 μg/ml) than the reference drug, amoxicillin (MIC = 128 μg/ml). Amoxicillin-p-methoxybenzoic acid (6b) had the best antibacterial activity in vivo (ED50 = 13.2496 μg/ml). The hybrid molecules of amoxicillin and derivatives of benzoic acid synthesized based on a diester structure can improve the activity of amoxicillin against Salmonella species and even improve the activity against MRSA.
Amoxicillin derivative as well as preparation method and application thereof
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Paragraph 0020; 0049-0050, (2020/08/02)
The invention provides an amoxicillin derivative with a structure shown as a formula I or a pharmaceutically and/or veterinary acceptable solvate of the amoxicillin derivative, wherein R is a hydrogenatom, an alkyl group, an amino group, a hydroxyl group, an amidino group, a guanidino group, a nitro group, a sulfonyl group or a group containing one of the alkyl group, the amino group, the hydroxyl group, the amidino group, the guanidino group, the nitro group and the sulfonyl group. According to the invention, two different lead compounds are connected together through a covalent bond to generate a synergistic effect, an addition effect or new pharmacological activity in vivo; benzoic acid is spliced to an amoxicillin side chain to generate a new amoxicillin-benzoic acid derivative, and the obtained new compound can broaden the antibacterial spectrum, has good antibacterial activity on gram-positive bacteria and gram-negative bacteria, and is effective for drug-resistant bacteria.
SULFONAMIDE DERIVATIVE AND PHARMACEUTICAL USE THEREOF
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Paragraph 0274; 0275; 0276, (2016/09/26)
Provided is a sulfonamide derivative represented by the following general formula (1) and having an α4 integrin inhibitory effect with high selectivity with a low effect on α4β1 and a high effect on α4β7, or a pharmaceutically acceptable salt thereof (in the general formula (1), A, B, D, E, R41, and a to h are as described in the description).
SULFONAMIDE DERIVATIVE AND MEDICINAL USE THEREOF
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Paragraph 1522-1523, (2015/02/25)
Provided are sulfonamide derivatives of a specific chemical structure in which a sulfonamide group having, as a substituent, a phenyl group or a heterocyclic group having a hetero atom(s) as a constituent element(s) is present at its terminal, and pharmaceutically acceptable salts thereof. These compounds are novel compounds having excellent α4 integrin-inhibitory action.
Total synthesis of heronapyrrole C
Ding, Xiao-Bo,Furkert, Daniel P.,Capon, Robert J.,Brimble, Margaret A.
supporting information, p. 378 - 381 (2014/04/03)
A flexible total synthesis of the 2-nitropyrrole-derived marine natural product, (+)-heronapyrrole C, is reported. The approach is based on regioselective access to key building blocks containing the rare 4-substituted 2-nitropyrrole motif. Sharpless asymmetric epoxidation and dihydroxylation and a Shi epoxidation were used to introduce the five stereogenic centers of the bis-THF-diol side chain. The N-benzoyloxymethyl (Boz) protecting group was crucial for functionalization of the 2-nitropyrrole moiety and enabling final deprotection under mild conditions.
MEROPENEM DERIVATIVES AND USES THEREOF
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Paragraph 000349; 000350, (2014/09/29)
The present invention provides novel derivative of β-lactam antibiotics, such as meropenem. The inventive compounds include compounds of Formula (I), and pharmaceutically acceptable salts, solvates, hydrates, polymorphs, co-crystals, tautomers, stereoisomers, isotopically labeled derivatives, and prodrugs thereof. Also provided are particles (e.g., nanoparticles) and pharmaceutical compositions thereof that are mucus penetrating. The inventive particles and pharmaceutical compositions may be useful in delivering an inventive compound to the respiratory tract of a subject. The invention further provides methods of using and kits including the inventive compounds, particles thereof, and/or pharmaceutical compositions thereof for treating and/or preventing a pulmonary disease (e.g., a respiratory tract infection).
Decoupled Roles for the Atypical, Bifurcated Binding Pocket of the ybfF Hydrolase
Ellis, Elizabeth E.,Adkins, Chinessa T.,Galovska, Natalie M.,Lavis, Luke D.,Johnson, R. Jeremy
, p. 1134 - 1144 (2013/07/26)
Serine hydrolases have diverse intracellular substrates, biological functions, and structural plasticity, and are thus important for biocatalyst design. Amongst serine hydrolases, the recently described ybfF enzyme family are promising novel biocatalysts with an unusual bifurcated substrate-binding cleft and the ability to recognize commercially relevant substrates. We characterized in detail the substrate selectivity of a novel ybfF enzyme from Vibrio cholerae (Vc-ybfF) by using a 21-member library of fluorogenic ester substrates. We assigned the roles of the two substrate-binding clefts in controlling the substrate selectivity and folded stability of Vc-ybfF by comprehensive substitution analysis. The overall substrate preference of Vc-ybfF was for short polar chains, but it retained significant activity with a range of cyclic and extended esters. This broad substrate specificity combined with the substitutional analysis demonstrates that the larger binding cleft controls the substrate specificity of Vc-ybfF. Key selectivity residues (Tyr116, Arg120, Tyr209) are also located at the larger binding pocket and control the substrate specificity profile. In the structure of ybfF the narrower binding cleft contains water molecules prepositioned for hydrolysis, but based on substitution this cleft showed only minimal contribution to catalysis. Instead, the residues surrounding the narrow binding cleft and at the entrance to the binding pocket contributed significantly to the folded stability of Vc-ybfF. The relative contributions of each cleft of the binding pocket to the catalytic activity and folded stability of Vc-ybfF provide a valuable map for designing future biocatalysts based on the ybfF scaffold.
Synthesis of acyloxyalkyl esters of thiocarbonic and dithiocarbamic acids
Mustafaev,Kulieva,Mustafaev,Kulibekova,Kakhramanova,Safarova,Novotorzhina
, p. 198 - 203 (2013/07/25)
Reactions of acyloxyalkyl chloride with alkaline salts of alkylxanthic, butyltrithiocarbonic, and diethyldithiocarbamic acids afforded a series of acyloxyalkyl esters of various nature and positions of the acyl groups in the molecule.
RODENTICIDAL NORBORMIDE ANALOGUES
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Page/Page column 77, (2013/09/26)
The present invention relates to norbormide analogues having rodenticidal activity; rodenticidal compositions comprising the analogues; uses of the analogues as rodenticides; uses of the analogues in the manufacture of rodenticidal compositions; and methods for controlling rodents using the compositions.
