New hydrazide-hydrazones of isonicotinic acid: synthesis, lipophilicity and in vitro antimicrobial screening

被引:30
|
作者
Popiolek, Lukasz [1 ]
Biernasiuk, Anna [2 ]
Berecka, Anna [3 ]
Gumieniczek, Anna [3 ]
Malm, Anna [2 ]
Wujec, Monika [1 ]
机构
[1] Med Univ Lublin, Dept Organ Chem, Fac Pharm, Lublin, Poland
[2] Med Univ Lublin, Dept Pharmaceut Microbiol, Fac Pharm, Lublin, Poland
[3] Med Univ Lublin, Dept Med Chem, Fac Pharm, Lublin, Poland
关键词
antibacterial activity; antifungal activity; hydrazide-hydrazone; MBC; MIC; ANTIMYCOBACTERIAL ACTIVITY; DERIVATIVES; DESIGN; DOCKING; ANALOGS; AGENTS;
D O I
10.1111/cbdd.13158
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
This study describes the synthesis, lipophilicity and in vitro antimicrobial assays of 15 new hydrazide-hydrazones of isonicotinic acid. New derivatives were obtained on the basis of the condensation reaction of isonicotinic acid hydrazide with different aromatic aldehydes. The chemical structure of synthesized compounds was confirmed by spectral methods. Experimental lipophilicity of new isonicotinic acid derivatives was determined using reversed-phase thin-layer chromatography. All synthesized compounds were subjected to in vitro antimicrobial assays against reference strains of Gram-positive bacteria, Gram-negative bacteria and fungi belonging to Candida spp. Some of the synthesized hydrazide-hydrazones proved to be significant antibacterial compounds and more potent than commonly used chemotherapeutic agents.
引用
收藏
页码:915 / 923
页数:9
相关论文
共 50 条
  • [21] Synthesis of some new hydrazide-hydrazones, thiosemicarbazides and thiazolidinones as possible antimicrobials
    Gursoy, A
    Terzioglu, N
    Otuk, G
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1997, 32 (09) : 753 - 757
  • [22] Searching for novel antimicrobial agents among hydrazide-hydrazones of 4-iodosalicylic acid
    Popiolek, Lukasz
    Tuszy, Katarzyna
    Biernasiuk, Anna
    BIOMEDICINE & PHARMACOTHERAPY, 2022, 153
  • [23] Synthesis and antituberculosis activity of indole-pyridine derived hydrazides, hydrazide-hydrazones, and thiosemicarbazones
    Velezheva, Valeriya
    Brennan, Patrick
    Ivanov, Pavel
    Kornienko, Albert
    Lyubimov, Sergey
    Kazarian, Konstantin
    Nikonenko, Boris
    Majorov, Konstantin
    Apt, Alexander
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2016, 26 (03) : 978 - 985
  • [24] Synthesis of some new hydrazide-hydrazones related to isatin and its Mannich and Schiff bases
    Afsah, Elsayed M.
    Elmorsy, Saad S.
    Abdelmageed, Soha M.
    Zaki, Zaki E.
    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2016, 71 (11): : 1147 - 1157
  • [25] Hydrazide-hydrazones as novel antioxidants - in vitro, molecular docking and DFT studies
    Mateev, Emilio
    Muhammed, Muhammed Tilahun
    Irfan, Ali
    Sharma, Shubham
    Georgieva, Maya
    Zlatkov, Alexander
    PHARMACIA, 2024, 71
  • [26] Isonicotinic acid hydrazide derivatives: synthesis, antimicrobial activity, and QSAR studies
    Judge, Vikramjeet
    Narasimhan, Balasubramanian
    Ahuja, Munish
    Sriram, Dharmarajan
    Yogeeswari, Perumal
    De Clercq, Erik
    Pannecouque, Christophe
    Balzarini, Jan
    MEDICINAL CHEMISTRY RESEARCH, 2012, 21 (07) : 1451 - 1470
  • [27] Synthesis and in vitro Antimicrobial Activity of Nalidixic Acid Hydrazones
    Popiolek, Lukasz
    Biernasiuk, Anna
    Malm, Anna
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2016, 53 (05) : 1589 - 1594
  • [28] Synthesis of Tolmetin Hydrazide-Hydrazones and Discovery of a Potent Apoptosis Inducer in Colon Cancer Cells
    Kucukguzel, S. Guniz
    Koc, Derya
    Cikla-Suzgun, Pelin
    Ozsavci, Derya
    Bingol-Ozakpinar, Ozlem
    Mega-Tiber, Pinar
    Orun, Oya
    Erzincan, Pinar
    Sag-Erdem, Safiye
    Sahin, Fikrettin
    ARCHIV DER PHARMAZIE, 2015, 348 (10) : 730 - 742
  • [29] Synthesis, characterization and anticancer activity of novel hydrazide-hydrazones derived from ethyl paraben
    Han, M. Ihsan
    Atalay, Pinar
    Imamoglu, Nalan
    Kucukguzel, S. Guniz
    JOURNAL OF RESEARCH IN PHARMACY, 2020, 24 (03): : 341 - 349
  • [30] New hydrazide-hydrazones and 1,3-thiazolidin-4-ones with 3-hydroxy-2-naphthoic moiety: Synthesis, in vitro and in vivo studies
    Popiolek, Lukasz
    Piatkowska-Chmiel, Iwona
    Gawronska-Grzywacz, Monika
    Biernasiuk, Anna
    Izdebska, Magdalena
    Herbet, Mariola
    Sysa, Marcin
    Malm, Anna
    Dudka, Jarostaw
    Wujec, Monika
    BIOMEDICINE & PHARMACOTHERAPY, 2018, 103 : 1337 - 1347