- Anti-biofilm effect of novel thiazole acid analogs against Pseudomonas aeruginosa through IQS pathways
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IQS has been proven to be a new quorum sensing (QS) system against bacterial biofilm formation, which is activated in the common phosphate-limiting environment of infected tissues taking over the central las system. Up to now, numerous biofilm inhibitors which function by affecting traditional QS system have been reported. However, no compound has been reported to exert anti-biofilm activity through IQS system. Herein, various novel IQS derivatives were synthesized by the reaction of thiazole-4-carboxylic acid with different linear alcohols (R-OH) or amines (R-NH2). IQS derivatives with four carbon chain length of R group were found to present the best biofilm inhibition activity. Compound B-11 as the model molecule was observed to inhibit biofilm formation only under phosphate-limiting condition, and increase in B-11 concentration significantly reduced the expression of rhlA-gfp and pqsA-gfp, but lasB-gfp. Moreover, B-11 reduced production of virulence factors of rhamnolipid and pyocyanin under phosphate limitation. These observations indicated that the synthesized compounds possessed the anti-biofilm activity through IQS pathways rather than traditional QS pathways, which pave a path for future molecular design against bacterial biofilm formation.
- Li, Shengrong,Chen, Siyu,Fan, Jilin,Cao, Zhen,Ouyang, Weihao,Tong, Ning,Hu, Xin,Hu, Jie,Li, Peishan,Feng, Zifeng,Huang, Xi,Li, Yuying,Xie, Mingshan,He, Ruikun,Jian, Jingyi,Wu, Biyuan,Xu, Chen,Wu, Weijian,Guo, Jialiang,Lin, Jing,Sun, Pinghua
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Read Online
- Method for preparing thiazole-4-formic acid
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The invention discloses a method for preparing thiazole-4-formic acid. By the aid of the method, the problems of relatively high prices of raw materials used in old processes for thiabendazole which is one of important traditional pesticide and bactericide varieties and low yield of the thiabendazole can be solved. The method includes steps of generating thiazolidine-4-formic acid from L-cysteinehydrochloride, formaldehyde and pyridine; carrying out reaction on the thiazolidine-4-formic acid, methyl alcohol and HCl gas to generate thiazolidine-4-methyl formate; carrying out reaction on the thiazolidine-4-methyl formate, acetonitrile and MnO2 to generate thiazole-4-methyl formate; hydrolyzing the thiazole-4-methyl formate under the effect of sodium hydroxide to obtain the thiazole-4-formicacid which is a product. The method has the advantages of simple process synthetic route, mild reaction condition, low cost, environmental protection, safety, excellent application prospect, good social benefit and high economic benefit.
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Paragraph 0021; 0026-0027; 0031; 0036-0037; 0041; 0046-0047
(2019/04/17)
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- Mechanism selection for regiocontrol in base-assisted, palladium-catalysed direct C-H coupling with halides: First approach for oxazole- and thiazole-4-carboxylates
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Both base-assisted non-concerted metallation-deprotonation (nCMD) and concerted metallation-deprotonation (CMD) have been identified as two potent operating mechanisms in palladium-catalysed direct C-H coupling of oxazole and thiazole-4-carboxylate esters
- Théveau, Laure,Verrier, Cécile,Lassalas, Pierrik,Martin, Thibaut,Dupas, Georges,Querolle, Olivier,Van Hijfte, Luc,Marsais, Francis,Hoarau, Christophe
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supporting information; experimental part
p. 14450 - 14463
(2012/01/15)
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- Direct C-2 arylation of alkyl 4-thiazolecarboxylates: New insights in synthesis of heterocyclic core of thiopeptide antibiotics
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(Chemical Equation Presented) The Pd(0)-catalyzed regioselective C-2 (hetero)arylation of tert-butyl 4-thiazolecarboxylate with a broad (hetero)aryl halide is reported, including the direct coupling of pyridinyl halides. The process has allowed the preparation of valuable 2-pyridynyl-4- thiazolecarboxylates which are components of the complex heterocyclic core of thiopeptides antibiotics. As a first application, a synthesis of a tert-butyl sulfomycinamate thio-analogue from tert-butyl 4-thiazolecarboxylate is here described through a three-step direct pyridinylation, halogenation, and Stille cross-coupling sequence.
- Martin, Thibaut,Verrier, Cecile,Hoarau, Christophe,Marsais, Francis
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supporting information; experimental part
p. 2909 - 2912
(2009/05/30)
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- Synthesis of thiazole compounds via lithiation: An unexpected rearrangement
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A novel rearrangement was discovered during an investigation of the lithium-bromine exchange reactions of bromothiazole derivatives and their subsequent reactions with various electrophiles.
- Ross Kelly,Lang, Fengrui
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p. 9293 - 9296
(2007/10/02)
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- A FACILE SYNTHETIC APPROACH TO THE FRAGMENT D OF ANTIBIOTIC NOSIHEPTIDE, 2--THIAZOLE-4-CARBOXYLIC ACID
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The lactam corresponding to fragment D of a polypeptide antibiotic nosiheptide was prepared via oxidation of the corresponding thiazolidine-4-carboxylate obtained by the condensation of 2-azido-2,3-dideoxy-D-threo-pentoalduronate with L-cysteine methyl ester.
- Iwakawa, Masaharu,Kobayashi, Yasunobu,Ikuta, Shun-ichi,Yoshimura, Juji
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p. 1975 - 1978
(2007/10/02)
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