1-benzylidene-2-(4-(4-methoxyphenyl)thiazol-2-yl)hydrazine | 4871-27-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-benzylidene-2-(4-(4-methoxyphenyl)thiazol-2-yl)hydrazine
• 英文别名: benzaldehyde [4-(4-methoxy-phenyl)-thiazol-2-yl]-hydrazone；N-Benzylidene-N'-<4-(4-methoxy-phenyl)-thiazol-2-yl>-hydrazine；N-(benzylideneamino)-4-(4-methoxyphenyl)-1,3-thiazol-2-amine
• CAS: 4871-27-6
• 化学式: C₁₇H₁₅N₃OS
• 分子量: 309.392
• InChiKey: JQBWAZBCWVZAIP-UHFFFAOYSA-N

物化性质

• 熔点：
  189-190 °C (decomp)(Solvent: Chloroform)
• 沸点：
  495.2±47.0 °C(predicted)
• 密度：
  1.21±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  74.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  苯甲醛 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 1.5h， 生成 1-benzylidene-2-(4-(4-methoxyphenyl)thiazol-2-yl)hydrazine
  参考文献：
  名称：

  噻唑腙衍生物的抗氧化和抗酪氨酸酶活性的合成、评价及其在鲜切马铃薯防褐变中的应用

  摘要：

  酪氨酸酶是黑色素生物合成中的关键酶，黑色素是导致食物褐变和许多皮肤病的原因。为了开发具有双重抗氧化和抗酪氨酸酶能力的新型抗褐变剂，合成了一系列30种噻唑腙衍生物。在制备的分子中，发现6和30是最有效的酪氨酸酶抑制剂，其 IC 50值与曲酸相当。有趣的是，6在制备的分子中也具有最高的自由基清除活性。抑制动力学研究表明6是一种非竞争性抑制剂，而30竞争性抑制酪氨酸酶。鲜切马铃薯片的抗褐变试验表明，6和30是有效的抗褐变剂，其能力与曲酸一样高。自由基清除和酪氨酸酶抑制的机制已在计算机中使用计算动力学、分子对接和分子动力学模拟进行了全面研究。

  DOI：

  10.1016/j.foodchem.2023.135745

文献信息

• Synthesis, anti-bacterial and anti-fungal activities of some novel Schiff bases containing 2,4-disubstituted thiazole ring
  作者：S.K. Bharti、G. Nath、R. Tilak、S.K. Singh

  DOI：10.1016/j.ejmech.2009.11.008

  日期：2010.2

  antimicrobial activities. The structures of synthesized compounds were established by spectroscopic (FT-IR, 1H NMR, 13C NMR, Mass) and elemental analyses. Both the anti-bacterial and anti-fungal activities with MIC values of compounds were evaluated. The results of anti-bacterial screening reveal that among all the compounds screened eight compounds showed moderate to good anti-bacterial activity while ten

  一系列的亚芳基-2-（4-（4-（4-甲氧基/溴苯基）噻唑-2-基）肼（4a – z）和1-（4-（4-甲氧基/溴苯基）噻唑-2-基）-2合成了-cyclohexydenne / cyclopentylidene肼（5a – b / 6a – b），并对其抗菌性能进行了表征和筛选。通过光谱（FT-IR，1 H NMR，1313 C NMR，质量）和元素分析。用化合物的MIC值评估了抗菌和抗真菌活性。抗菌筛选结果表明，在筛选出的所有化合物中，有八种化合物表现出中等至良好的抗菌活性，而新合成的化合物中有十种表现出良好至优异的抗真菌活性。在测试的化合物中，MIC值在6.25–25μg/ ml范围内的最有效化合物是针对三种真菌菌株viz的4a，4n，4z，5a，5b，6a和6b。白色念珠菌，新型隐球菌和黄曲霉。
• Eco-Friendly One-Pot Synthesis of 2,4-Disubstituted Thiazoles by Grinding Under Catalyst- and Solvent-Free Conditions
  作者：Quansehng Ding、Dongjian Zhu、Huile Jin、Jiuxi Chen、Jinchang Ding、Huayue Wu

  DOI：10.1080/10426507.2010.492366

  日期：2011.1.31

  Abstract An efficient and facile synthesis of 2,4-disubstituted thiazoles is achieved by a one-pot reaction of aldehydes and α-bromoketones with thiosemicarbazide by grinding under catalyst- and solvent-free conditions. This method has notable advantages in terms of simple workup, neat conditions, high yield, reasonably rapid reaction rate, and environmental friendliness. Supplemental materials are

  摘要 通过醛和α-溴酮与氨基硫脲的一锅反应，在无催化剂和无溶剂的条件下研磨，实现了2,4-二取代噻唑的高效、简便合成。该方法具有后处理简单、条件整洁、收率高、反应速度合理、环境友好等显着优势。补充材料可用于本文。转至出版商在线版的磷、硫和硅及相关元素，查看免费的补充文件。图形概要
• Thiazole compounds with activity against Cryptococcus gattii and Cryptococcus neoformans in vitro
  作者：Nívea Pereira de Sá、Cleudiomar Inácio Lino、Nayara Cristina Fonseca、Beatriz Martins Borelli、Jonas Pereira Ramos、Elaine Maria Souza-Fagundes、Carlos Augusto Rosa、Daniel Assis Santos、Renata Barbosa de Oliveira、Susana Johann

  DOI：10.1016/j.ejmech.2015.07.032

  日期：2015.9

  Human cryptococcosis can occur as a primary or opportunistic infection and develop as an acute, subacute, or chronic, systemic infection involving different host organs. We evaluated the antifungal activity of thirteen compounds against Cryptococcus gattii and Cryptococcus neoformans in vitro, by assessing the toxicity of the compounds showing the greatest antifungal activity in VERO cells and murine macrophages. From these results, four compounds were considered promising for further studies because they displayed low cytotoxicity and significant antifungal activity. The heterocyclic compounds 1b, 1c, 1d, and 1m have antifungal activity levels between that of amphotericin B and fluconazole in vitro. The death curve of Cryptococcus spp. treated with these four compounds was similar to the curve obtained for amphotericin B, in that we observed a significant reduction in cell viability within the first 24 h of treatment. Additionally, we found that there was no effect when these compounds were combined with amphotericin and fluconazole, except for 1c, which antagonized the effect of amphotericin B against C. gattii, also reflected in the reduction of the post-antifungal effect (PAFE); however, this interaction did not alter the ergosterol content. The results shown in this paper reveal the discovery of novel thiazole compounds, which are easy to synthesize, and with potentially exhibit antifungal activity, and display low cytotoxicity in normal mammalian cells. These compounds can be used as prototypes for the design of new antifungal drugs against C gattii and C neoformans. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Design, synthesis and biological evaluation of some novel benzylidene-2-(4-phenylthiazol-2-yl) hydrazines as potential anti-inflammatory agents
  作者：Sanjay Kumar Bharti、Sushil Kumar Singh

  DOI：10.1007/s00044-013-0708-z

  日期：2014.2

  A series of substituted benzylidene-2-(4-phenylthiazol-2-yl) hydrazines (2a-q) have been synthesized, characterized and evaluated for their anti-inflammatory activity by carrageenin-induced hind paw edema (acute inflammation) and cotton pellet granuloma (chronic inflammation) methods in rats. In carrageenin-induced hind paw edema method, compounds 2a, 2b, 2c, 2d, 2h, 2k and 2p at a dose of 20 mg kg(-1) body weight, p.o. showed excellent inhibitions (51.80-86.74 %) in between 1 and 4 h. Similarly, in cotton pellet granuloma method, compounds 2a, 2b, 2c, 2d, 2h, 2k and 2p at a dose of 20 mg kg(-1) body weight, p.o. inhibited the granuloma formation (71.71-90.19 % inhibition) which was comparable to that of standard drug, ibuprofen (90.36 % inhibition of paw volume at 3 h and 94.02 % inhibition of granuloma formation). Structure activity relationship studies showed excellent activity of the compounds containing electron withdrawing group (fluoro, chloro, bromo or nitro) in phenyl ring at C2 and/or C4 position of thiazole ring.
• Bulka,E.; Dinse,H.-D., Zeitschrift fur Chemie, 1965, vol. 5, p. 376 - 378
  作者：Bulka,E.、Dinse,H.-D.

  DOI：——

  日期：——