2623-33-8Relevant articles and documents
Structure of a monoclinic polymorph of N-[4-(acetyloxy)-phenyl]acetamide, a prodrug of acetaminophen
Caira,De Wet,Gerber
, p. 175 - 178 (1999)
The preparation, single crystal x-ray structure and the computed powder XRD pattern of a monoclinic polymorph of N-[4-(acetyloxy)phenyl]acetamide, a prodrug of acetaminophen, are reported. The polymorph crystallizes in the space group P21/n with Z = 4 and unit cell dimensions a = 7.219(2), b = 8.015(2), c = 16.575(2) A, β = 92.07(1)°, and V = 958.4(4) A3. Infinite spiral molecular arrays result from intermolecular head-to-tail hydrogen bonding between the amidic H atom of one molecule and the acetoxy carbonyl oxygen atom of a 21-related molecule.
Molecules with: O -acetyl group protect protein glycation by acetylating lysine residues
Vannuruswamy, Garikapati,Jagadeeshaprasad, Mashanipalya G.,Kashinath,Kesavan, Suresh K.,Bhat, Shweta,Korwar, Arvind M.,Chougale, Ashok D.,Boppana, Ramanamurthy,Reddy, D. Srinivasa,Kulkarni, Mahesh J.
, p. 65572 - 65578 (2016)
Pharmaceutical intervention for reduction of advanced glycation end products (AGEs) is considered as a therapeutic strategy to attenuate the pathogenesis of diabetes. Many molecules have been reported to possess antiglycation activity, one such example is acetylsalicylic acid (aspirin). It protects proteins from glycation by acetylating the lysine residues. Therefore, in this study we have synthesized and screened molecules containing free N-acetyl, O-acetyl and acetophenone groups. All the selected molecules in this study showed glycation inhibition but interestingly, only molecules with O-acetyl but not N-acetyl and acetophenone groups were capable of acetylating lysine residue. Furthermore, we have demonstrated that pre-acetylation or aspirin treatment prior to the induction of diabetes helps in reducing HbA1c and AGE formation in the streptozotocin induced diabetic mice. Hence pre-acetylation may have an additional therapeutic efficacy of reducing AGE levels in vivo. Incorporation of O-acetyl group into anti-diabetic molecules could be a useful strategy, as it may have an additive effect in reducing AGEs. Identification of such novel acetylating agents represents a new area in the drug discovery process.
Method for diacetate intermediate 5 - acetamide group -2 - (2, 3 - epoxypropoxy) acetophenone
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Paragraph 0022; 0026-0027; 0029-0030; 0032-0033; 0035-0036.., (2021/11/14)
The invention belongs to the field of organic photochemical and drug intermediate chemistry. The invention particularly relates to a method for synthesizing diacetate intermediate - acetamide group 5 - (-2 - 2 epoxypropoxy) acetophenone containing acetylated 3 - photochemical rearrangement reaction in series. The reactant is cooled to the polar organic solvent, Fries rearrangement is carried out directly by ultraviolet - visible light irradiation with specific wavelength, and the intermediate Fries acetyl 2 -4 - acetyl aminophenol is obtained by heating and evaporating the solvent after the reaction is finished. Sodium hydroxide was added to prepare the phenol salt. Then, an intermediate 5 - acetamide group -2 - (2, 3 - epoxypropoxy) acetophenone was obtained by reaction with epichlorohydrin. The tandem type synthesis method disclosed by the invention is simple and feasible, and low-toxicity, high-efficiency and cheap green chemical reagents are used in the synthesis process.
An Electrochemical Beckmann Rearrangement: Traditional Reaction via Modern Radical Mechanism
Tang, Li,Wang, Zhi-Lv,He, Yan-Hong,Guan, Zhi
, p. 4929 - 4936 (2020/08/21)
Abstract: Electrosynthesis as a potential means of introducing heteroatoms into the carbon framework is rarely studied. Herein, the electrochemical Beckmann rearrangement, i. e. the direct electrolysis of ketoximes to amides, is presented for the first time. Using a constant current as the driving force, the reaction can be easily carried out under neutral conditions at room temperature. Based on a series of mechanistic studies, a novel radical Beckmann rearrangement mechanism is proposed. This electrochemical Beckmann rearrangement does not follow the trans-migration rule of the classical Beckmann rearrangement.