1918-77-0Relevant articles and documents
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Blanchette,Brown
, p. 1066 (1952)
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Assessing and utilizing esterase specificity in antimicrobial prodrug development
Hetrick, Kenton J.,Raines, Ronald T.
, (2021/12/30)
As a class of enzymes, esterases have been investigated for decades and have found use in industrial processes, synthetic organic chemistry, and elsewhere. Esters are functional groups composed of an alcohol moiety and a carboxylic acid moiety. Although much work has explored the influence of the carboxyl moiety of an ester on its susceptibility to esterases, little work has explored the influence of the alcohol moiety. Here, we describe an in vitro methodology to explore the influence of changing the alcohol moiety of an ester on its enzymatic hydrolysis, including strategies for analyzing such data. We then describe leveraging data from these assays to develop targeted antimicrobial prodrugs that activate in certain species due to the discriminatory activity of species-specific esterases. We envisage the potential of genomics and machine learning to further these efforts. Finally, we anticipate the potential future uses of these ideas, including developing targeted anti-cancer compounds.
Oxidation of Alkynyl Boronates to Carboxylic Acids, Esters, and Amides
Li, Chenchen,Li, Ruoling,Zhang, Bing,Zhao, Pei,Zhao, Wanxiang
, p. 10913 - 10917 (2020/05/25)
A general efficient protocol was developed for the synthesis of carboxylic acids, esters, and amides through oxidation of alkynyl boronates, generated directly from terminal alkynes. This protocol represents the first example of C(sp)?B bond oxidation. This approach displays a broad substrate scope, including aryl and alkyl alkynes, and exhibits excellent functional group tolerance. Water, primary and secondary alcohols, and amines are suitable nucleophiles for this transformation. Notably, amino acids and peptides can be used as nucleophiles, providing an efficient method for the synthesis and modification of peptides. The practicability of this methodology was further highlighted by the preparation of pharmaceutical molecules.
Preparation method of 2-thiopheneacetyl chloride
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Paragraph 0034-0037; 0041-0044; 0046-0049; 0051-0054; 0056, (2020/08/30)
The invention discloses a preparation method of 2-thiopheneacetyl chloride, and belongs to the technical field of chemical synthesis. The preparation method comprises the following steps: (1) dissolving 2-thiopheneethanol in an organic solvent, and reacting at 50-120 DEG C under the action of a solid acid catalyst, an alkali and an oxidant to prepare 2-thiopheneacetic acid, wherein the oxidant isoxygen or hydrogen peroxide; and (2) dissolving 2-thiopheneacetic acid in an organic solvent, and dropwise adding thionyl chloride to carry out an acylating chlorination reaction by taking an alkalineionic liquid as a catalyst so as to prepare 2-thiopheneacetyl chloride. The preparation method is simple in route, easy in obtaining of raw materials, mild in reaction conditions, and capable of realizing few byproducts and easy purification and separation due to adoption of oxygen or hydrogen peroxide as the oxidant in synthesis of 2-thiopheneacetic acid; and when the acylating chlorination reaction of 2-thiopheneacetic acid is carried out, the basic ionic liquid is adopted as the catalyst, the reaction process is stable and easy to control, the product yield is high, few byproducts are produced, so the method is an efficient and green synthesis process.