Chemical properties and immunotropic activity of the products from reaction of N-(6-methyl-2,4-dioxo-1,2,3,4-tetrahydro-5H-pyrimidinesulfone)-N′-isonicotinoylhydrazide with acids and bases in aqueous media

被引:0
|
作者
E. S. Ryzhova
D. A. Panteleev
Yu. V. Chudetskaya
A. A. Volkov
N. B. Mel’nikova
M. V. Gulenova
V. K. Osmanov
A. V. Borisov
机构
[1] Nizhni Novgorod State Medical Academy,
[2] Nizhni Novgorod State Technical University,undefined
来源
关键词
tautomerism; pyridine and pyrimidine derivatives; acid–base reactions; organic acids; hyaluronic acid; -(hydroxymethyl)aminomethane; triethanolamine; specific immunotropic activity;
D O I
暂无
中图分类号
学科分类号
摘要
The effect of tautomerism on the structure of products from the reaction of N-(6-methyl-2,4-dioxo-1,2,3,4-tetrahydro-5H-pyrimidinesulfone)-N′-isonicotinoylhydrazide (kristafon) with acids (hydrochloric, phosphoric, acetic, oxalic, succinic, citric, hyaluronic) and bases [sodium hydroxide, triethanolamine, tris-(hydroxymethyl)aminomethane] in aqueous media has been studied using UV, IR, PMR, and 13C NMR spectroscopy techniques. The properties of kristafon are compared to those of analogous compounds containing pyridine (isonicotine hydrazide, sulfotolylisonicotine hydrazide) and pyrimidine [bis-p-(2,4-dioxo-6-methylpyrimidinyl-5-sulfonamino)-diphenylsulfone] fragments in acid–base media. It is shown that the immunotropic activity of kristafon phosphate and kristafon are improved in hyaluronic acid solution.
引用
收藏
页码:205 / 212
页数:7
相关论文
共 34 条
  • [21] SYNTHESIS OF BIOLOGICALLY POTENT ALKOXYPHTHALIMIDO PLUGGED N-(2,4-DIOXO-1,4-DIHYDROQUINAZOLIN-3(2H)-YL)-4-OXO-4H-BENZO[4,5]THIAZOLO[3,2-A]PYRIMIDINE-3-CARBOXAMIDE VIA GOULD JACOBS REACTION
    Prajapat, Prakash
    Pappula, Venkata Narayana
    Vaghani, Hasit
    Agarwal, Shikha
    Samota, Jayanti
    Talesara, Ganpat L.
    HETEROCYCLIC LETTERS, 2021, 11 (01): : 63 - 72
  • [22] Synthesis and herbicidal activity of N-{2-chloro-5-[3-methyl-2,6-dioxo-4-trifluoromethyl-2,3-dihydropyrimidin-1(6-H)-yl]phenyl} amides
    Huang, Ming-Zhi
    Zhang, Quan
    Ren, Ye-Guo
    Lei, Man-Xiang
    Huang, Lu
    Ren, Jing
    Yang, Guang-Fu
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2006, 26 (11) : 1539 - 1543
  • [23] Unprecedented solid-state chemical reaction - from(C3N2H5)3SbBr6•H2O to (C3N2H5)5Sb2Br11; polimorphism of substrate and products.
    Gagor, A.
    Piecha, A.
    Jakubas, R.
    Pietraszko, A.
    ACTA CRYSTALLOGRAPHICA A-FOUNDATION AND ADVANCES, 2010, 66 : S277 - S277
  • [24] Synthesis of 11-bromo-9-methyl-6-methylene-3-methylthio-5,6,9,10-tetrahydro-8H-[1,2,4]triazolo[3′,4′:3,4]pyrazino[1,2-c]pyrimidine-8,10-dione from 4-allyl-1-(3-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidinyl-6-carbonyl)thiosemicarbazide
    Myakushkene, G
    Vainilavichyus, P
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1999, (01): : 67 - 70
  • [25] Catalytic synthesis and antimicrobial activity of N-(3-chloro-2-oxo-4-phenylazetidin-1-yl)-4-(1H-indol-3-yl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxamides
    Desai, Nisheeth C.
    Bhatt, Malay J.
    HETEROCYCLIC COMMUNICATIONS, 2016, 22 (03) : 131 - 136
  • [26] Synthesis of alkyl 6-methyl-4-(2-trifluoromethylphenyl)-1,2,3,4-tetrahydro-2H-pyrimidine-2-one-5-carboxylates possessing a N-3 nitro substituent to determine calcium channel modulation structure-activity relationships
    Kaur, Kujeet
    Knaus, Edward E.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2007, 44 (03) : 669 - 672
  • [27] Synthesis and Herbicidal Activity of Novel N-(2-Fluoro-5(3-methyl-2,6-dioxo-4-(trifluoromethyl)-2,3-dihydro-pyrimidin-1(6H)-yl)phenyl)-2-phenoxyacetamide Derivatives
    Wu Daoxin
    Sun Jiong
    Huang Mingzhi
    Mo Hongbo
    Wang Xiaoguang
    Li Hongwei
    Ren Yeguo
    Hu Zhibing
    He Lian
    Yin Dulin
    CHINESE JOURNAL OF CHEMISTRY, 2011, 29 (11) : 2401 - 2406
  • [28] Crystal structure of ethyl 5"-(2,4-dichloroyphenyl)-1′-methyl-4-carboxylic acid methyl ester-2,3"-dioxo-2,3,2",3"-tetrahydro-1H-indole-3-spiro-2′-pyrrolidine-3′-spiro-2"-thiazolo[3",2"-a]-pyrimidine-6"-carboxylate, C29H26Cl2N4O6S
    Ling, Yulin
    Li, Xiaofang
    ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES, 2009, 224 (02): : 335 - 336
  • [29] 2-({6-[(3R)-3-amino-3-methylpiperidine-1-yl]-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-5H-pyrrolo[3,2-d]pyrimidine-5-yl}methyl)-4-fluorobenzonitrile (DSR-12727): A potent, orally active dipeptidyl peptidase IV inhibitor without mechanism-based inactivation of CYP3A
    Nishio, Yukihiro
    Kimura, Hidenori
    Sawada, Naoyuki
    Sugaru, Eiji
    Horiguchi, Masakuni
    Ono, Michiko
    Furuta, Yudai
    Sakai, Mutsuko
    Masui, Yumi
    Otani, Misato
    Hashizuka, Takahiko
    Honda, Yayoi
    Deguchi, Jiro
    Nakagawa, Tsutomu
    Nakahira, Hiroyuki
    BIOORGANIC & MEDICINAL CHEMISTRY, 2011, 19 (18) : 5490 - 5499
  • [30] The Study of the Structure-Diuretic Activity Relationship in a Series of New N-(Arylalkyl)-6-hydroxy-2-methyl-4-oxo-2,4-dihydro-1H-pyrrolo-[3,2,1-ij]quinoline-5-carboxamides
    Ukrainets, Igor V.
    Golik, Mykola Y.
    Sidorenko, Lyudmila V.
    Korniyenko, Valentina I.
    Grinevich, Lina A.
    Sim, Galina
    Kryvanych, Olga V.
    SCIENTIA PHARMACEUTICA, 2018, 86 (03)