Sharma Shashi, Tuli Hardeep Singh, Varol Mehmet, Agarwal Pallvi, Rani Anita, Abbas Zahoor, Kumar Manoj
Department of Chemistry, Dyal Singh College, Karnal, Haryana, India.
Department of Biotechnology, Maharishi Markandeshwar (Deemed to be) University, Mullana, Haryana, India.
Int J Health Sci (Qassim). 2022 Jul-Aug;16(4):3-12.
Microbial diseases are snowballing at an alarming proportion. Therefore, the intent of this study was to inspect the antimicrobial action of ferrocenyl-substituted pyrazole against various human pathogenic Gram-positive, Gram-negative, and fungal microbial strains. Pyrazoles have been recognized for over a century as a significant and bioactive class of heterocyclic compounds. The association of pyrazoles with a ferrocene moiety may give new class of compounds. The present study was designed to synthesize biological active ferrocenyl-substituted pyrazole through a novel route.
The anhydride of ferrocenyl-substituted pyrazole, namely, (S)-(3-(3-(carboxyamino)-3H-pyrazol-4-yl)cyclopenta-1,3-dien-1-yl)(cyclopenta-1,3-dien-1-yl)iron was synthesized using expansion cyclocondensation. FTIR, NMR, and GC-MS were performed to analyze the structure of the synthesized ferrocenyl-substituted pyrazole. Antimicrobial, DNA photo-cleaving, and anti-angiogenic activities of ferrocenyl-substituted compounds were studied.
Anhydride of (S)-(3-(3-(carboxyamino)-3H-pyrazol-4-yl)cyclopenta-1,3-dien-1-yl)(cyclopenta-1,3-dien-1-yl)iron obtained with yield of 87%. Spectral analysis confirmed the formation of anhydride. The synthesized compound was found to be biological active in the range of 85-95 μg/ml.
This study described the novel method for the synthesis of biologically active anhydride of ferrocenyl-substituted pyrazole. The study demonstrations that synthesized ferrocenyl-substituted pyrazole in today's situation is the encouraging antimicrobial mediator against the human pathogens. In addition, it may open new doors to initiate research against drug resistance bacteria with possible biomedical applications.
微生物疾病正以惊人的比例迅速增加。因此，本研究的目的是考察二茂铁基取代吡唑对各种人类致病革兰氏阳性菌、革兰氏阴性菌和真菌微生物菌株的抗菌作用。吡唑作为一类重要的具有生物活性的杂环化合物已被认可了一个多世纪。吡唑与二茂铁部分的结合可能产生新的化合物类别。本研究旨在通过一条新途径合成具有生物活性的二茂铁基取代吡唑。
采用扩环缩合反应合成了二茂铁基取代吡唑的酸酐，即(S)-(3-(3-(羧基氨基)-3H-吡唑-4-基)环戊-1,3-二烯-1-基)(环戊-1,3-二烯-1-基)铁。利用傅里叶变换红外光谱(FTIR)、核磁共振(NMR)和气相色谱-质谱联用(GC-MS)对合成的二茂铁基取代吡唑的结构进行了分析。研究了二茂铁基取代化合物的抗菌、DNA光裂解和抗血管生成活性。
得到(S)-(3-(3-(羧基氨基)-3H-吡唑-4-基)环戊-1,3-二烯-1-基)(环戊-1,3-二烯-1-基)铁的酸酐，产率为87%。光谱分析证实了酸酐的形成。发现合成的化合物在85-95μg/ml范围内具有生物活性。
本研究描述了一种合成具有生物活性的二茂铁基取代吡唑酸酐的新方法。该研究表明，在当今情况下，合成的二茂铁基取代吡唑是一种针对人类病原体的有前景的抗菌介质。此外，它可能为开展针对耐药细菌的研究以及可能的生物医学应用打开新的大门。
