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棓酰肼的精确常规合成与微波辅助合成。

Accurate conventional and microwave-assisted synthesis of galloyl hydrazide.

作者信息

Rabie Amgad M

机构信息

Department of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt.

出版信息

MethodsX. 2019 Nov 15;7:100737. doi: 10.1016/j.mex.2019.11.010. eCollection 2020.

Abstract

The usefulness of the structure of galloyl hydrazide (3,4,5-trihydroxybenzohydrazide, coded as in this article) as a privileged structural system in pharmaceutical organic and medicinal chemistry has prompted the advances of the further therapeutic potentials of this known antioxidant/antitumor compound and, in addition to that, it acts generally as a very important organic reaction intermediate for molecule planning (including synthesis of many important biologically active molecules), as it undergoes various types of chemical reactions. The data of the two synthetic methods (including the new green one), presented in this research article, provides sharp adequate chemical data about the challenging synthesis, separation (purification), and characterization of this compound. A new and very fast one-pot solventless greener microwave-assisted method of synthesis, in addition to the much slower old conventional one, is used in this present research; and followed by full precise purification and characterization (including chromatographic separation; physicochemical identification; IR, H-NMR, C-NMR, and mass spectroscopic analyses along with elemental analyses for structure elucidation) of . •Galloyl hydrazide is a very important and unique organic chemical intermediate with, mainly, antioxidant and anticancer biological activities.•Galloyl hydrazide synthesis in the previous literature is very challenging, confusing, not standardized, and without any consensus.•The main objective of this new research is to make two standard and fixed methods of synthesis (conventional and greener) of galloyl hydrazide through designing and constructing a new one-pot solventless greener microwave-assisted synthetic method, in addition to redesigning and qualifying the old traditional conventional heating one; both methods are followed by very accurate identification and characterization data (which can be referenced for the efficient reproducibility in the organic and pharmaceutical chemistry community) of galloyl hydrazide.

摘要

没食子酰肼(3,4,5-三羟基苯甲酰肼,本文中编码为 )的结构作为药物有机化学和药物化学中一种特殊的结构体系,其有效性推动了这种已知抗氧化剂/抗肿瘤化合物进一步治疗潜力的发展。此外,它通常作为分子设计(包括许多重要生物活性分子的合成)中非常重要的有机反应中间体,因为它能发生各种类型的化学反应。本研究文章中介绍的两种合成方法(包括新的绿色合成方法)的数据,为该化合物具有挑战性的合成、分离(纯化)和表征提供了充分准确的化学数据。本研究采用了一种新型且非常快速的无溶剂一锅法绿色微波辅助合成方法,以及传统的较慢的方法;随后对 进行了完全精确的纯化和表征(包括色谱分离、物理化学鉴定、红外光谱、氢核磁共振、碳核磁共振和质谱分析以及元素分析以阐明结构)。

•没食子酰肼是一种非常重要且独特的有机化学中间体,主要具有抗氧化和抗癌生物活性。

•先前文献中没食子酰肼合成极具挑战性、令人困惑、不规范且没有任何共识。

•这项新研究的主要目标是通过设计和构建一种新型无溶剂一锅法绿色微波辅助合成方法,以及重新设计和优化传统的传统加热合成方法,制定两种标准且固定的没食子酰肼合成方法(传统方法和绿色方法);两种方法之后都有非常准确的没食子酰肼鉴定和表征数据(可在有机化学和药物化学领域用于高效重现)。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c647/6997622/8333cba30cc3/fx1.jpg

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