Synthesis, structure and biological activity of hydrazones derived from 2- and 4-hydroxybenzoic acid hydrazides

被引：7

作者：

Nurkenov, Oralgazy A. ^{[1
,2
]}

Fazylov, Serik D. ^{[1
,3
]}

Satpaeva, Zhanarkul B. ^{[1
,3
]}

Seilkhanov, Tulegen M. ^{[4
]}

Turdybekov, Dastan M. ^{[3
]}

Mendibayeva, Anel Zh. ^{[1
,2
]}

Akhmetova, Saule B. ^{[5
]}

Shulgau, Zarina T. ^{[6
]}

Alkhimova, Larisa E. ^{[7
]}

Kulakov, Ivan V. ^{[1
]}

机构：

[1] Inst Organ Synth & Coal Chem Republ Kazakhstan, 1 Alikhanov St, Karaganda 100008, Kazakhstan

[2] Karaganda Ind Univ, 30 Republ Ave, Temirtau 101400, Kazakhstan

[3] Karaganda Buketov Univ, 28 Univ St, Karaganda 100028, Kazakhstan

[4] Ualikhanov Univ, 76 Abaya St, Kokshetau 020000, Kazakhstan

[5] Karaganda Med Univ, 40 Gogol St, Karaganda 100000, Kazakhstan

[6] Natl Ctr Biotechnol, 13-5 Kurgalzhynskoe Rd, Astana 010000, Kazakhstan

[7] Univ Tyumen, Ctr Nat Inspired Engn, 15a Perekopskaya St, Tyumen 625003, Russia

来源：

CHEMICAL DATA COLLECTIONS | 2023年 / 48卷

关键词：

Hydrazides of 2-and 4-hydroxybenzoic acids; Benzaldehydes; Hydrazones; X-ray diffraction analysis; Antimicrobial activity; HIRSHFELD SURFACE-ANALYSIS; SALICYLIC-ACID; DERIVATIVES; IDENTIFICATION; DOCKING; DFT;

D O I：

10.1016/j.cdc.2023.101089

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The condensation reaction of 4- and 2-hydroxybenzoic acid hydrazides with substituted benzaldehydes led to the formation of a series of hydrazones. The synthesis of hydrazones was carried out successfully in good yields. The structure of compounds was proved by spectral methods. The crystal structures of the methanol solvate of the (E)-N'-[4-(diethylamino)-benzylidene]-4-hydroxybenzohydrazide and the crystalline hydrate of the (E)-N'-[(2-hydroxy-4-diethylamino)-benzylidene]-4-hydroxybenzohydrazide were described with attention to conformational features and hydrogen bonding. The antimicrobial and antiradical activity of hydrazones was studied using molecular docking and in vitro assays.

引用

页数：13

共 56 条

[11] Avogadro: an advanced semantic chemical editor, visualization, and analysis platform [J].

Hanwell, Marcus D. ;

Curtis, Donald E. ;

Lonie, David C. ;

Vandermeersch, Tim ;

Zurek, Eva ;

Hutchison, Geoffrey R. .

JOURNAL OF CHEMINFORMATICS, 2012, 4

[12]

Hussein M.A., 2005, Bull. Pharm. Sci. Assiut Univ., V28, P131, DOI 10.21608/bfsa.2005.65240

[13] The enrichment ratio of atomic contacts in crystals, an indicator derived from the Hirshfeld surface analysis [J].

Jelsch, Christian ;

Ejsmont, Krzysztof ;

Huder, Loic .

IUCRJ, 2014, 1 :119-128

[14] Plant-Derived and Dietary Hydroxybenzoic Acids-A Comprehensive Study of Structural, Anti-/Pro-Oxidant, Lipophilic, Antimicrobial, and Cytotoxic Activity in MDA-MB-231 and MCF-7 Cell Lines [J].

Kalinowska, Monika ;

Golebiewska, Ewelina ;

Swiderski, Grzegorz ;

Meczynska-Wielgosz, Sylwia ;

Lewandowska, Hanna ;

Pietryczuk, Anna ;

Cudowski, Adam ;

Astel, Aleksander ;

Swislocka, Renata ;

Samsonowicz, Mariola ;

Zlowodzka, Anna Barbara ;

Priebe, Waldemar ;

Lewandowski, Wlodzimierz .

NUTRIENTS, 2021, 13 (09)

[15] Overall Content of Salicylic Acid and Salicylates in Food Available on the European Market [J].

Keszycka, Paulina K. ;

Szkop, Michal ;

Gajewska, Danuta .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2017, 65 (50) :11085-11091

[16] Synthesis of 4-Hydroxybenzoic Acid Derivatives in Escherichia coli [J].

Kim, Han ;

Kim, Song Yi ;

Sim, Geun Young ;

Ahn, Joong-Hoon .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2020, 68 (36) :9743-9749

[17] Molecular Insights into Function and Competitive Inhibition of Pseudomonas aeruginosa Multiple Virulence Factor Regulator [J].

Kitao, Tomoe ;

Lepine, Francois ;

Babloudi, Seda ;

Walte, Frederick ;

Steinbacher, Stefan ;

Maskos, Klaus ;

Blaesse, Michael ;

Negri, Michele ;

Pucci, Michael ;

Zahler, Bob ;

Felici, Antonio ;

Rahme, Laurence G. .

MBIO, 2018, 9 (01)

[18] Antituberculosis activity of hydrazones derived from 4-fluorobenzoic acid hydrazide [J].

Kocyigit-Kaymakcioglu, Bedia ;

Oruc-Emre, Emine Elcin ;

Unsalan, Seda ;

Rollas, Sevim .

MEDICINAL CHEMISTRY RESEARCH, 2009, 18 (04) :277-286

[19] Synthesis of the First Representatives of Thieno[3,2-c][1,7]naphthyridine Derivatives Based on 3-Amino-6-methyl-4-(2-thienyl)pyridin-2(1H )-one [J].

Kulakov, Ivan V. ;

Matsukevich, Mariya V. ;

Levin, Maxim L. ;

Palamarchuk, Irina V. ;

Seilkhanov, Tulegen M. ;

Fisyuk, Alexander S. .

SYNLETT, 2018, 29 (13) :1741-1744

[20] Synthesis, structure and biological activity 3-(arylmethyl) aminopyridine-2 (1H) -ones and 1H-pyrido[2,3-b][1,4]oxazin-2(3H)-ones [J].

Kulakov, Ivan, V ;

Palamarchuk, Irina, V ;

Shulgau, Zarina T. ;

Seilkhanov, Tulegen M. ;

Gatilov, Yuriy, V ;

Fisyuk, Alexander S. .

JOURNAL OF MOLECULAR STRUCTURE, 2018, 1166 :262-269

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