1-isatin-4-butyl-3-thiosemicarbazone | 92460-97-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-isatin-4-butyl-3-thiosemicarbazone
• CAS: 92460-97-4
• 化学式: C₁₃H₁₆N₄OS
• 分子量: 276.362
• InChiKey: FSTPQTUPBDIXJL-UHFFFAOYSA-N

物化性质

• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.61
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  65.52
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-溴-4'-硝基苯乙酮 、 1-isatin-4-butyl-3-thiosemicarbazone 在 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以99%的产率得到[2-(4-nitrophenyl)-2-oxoethyl] N'-butyl-N-[(2-oxoindol-3-yl)amino]carbamimidothioate
  参考文献：
  名称：

  Karah, Nilguen; Terzioglu, Nalan; Guersoy, Aysel, Arzneimittel-Forschung/Drug Research, 1998, vol. 48, # 7, p. 758 - 763

  摘要：

  DOI：
• 作为产物：
  描述：

  N-Butyl-thioformamid 在 一水合肼 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 1-isatin-4-butyl-3-thiosemicarbazone
  参考文献：
  名称：

  Insight on a new indolinone derivative as an orally bioavailable lead compound against renal cell carcinoma

  摘要：

  DOI：

  10.1016/j.bioorg.2021.104985

文献信息

• Syntheses of Some Substituted Isatin-β-thiosemicarbazones and Isatin-β-hydrazonothiazoline Derivatives as Potential Antiviral and Antimicrobial Agents
  作者：A.-Mohsen M. E. Omar、Nabil H. Eshba、Hassan M. Salama

  DOI：10.1002/ardp.19843170810

  日期：——

  A series of isatin‐β‐thiosemicarbazones and isatin‐β‐hydrazonothiazolines was synthesized by condensation of various isatin derivatives with N4‐substituted 3‐thiosemicarbazides and cyclization of the products by phenacyl bromides. The products showed high toxicity at lower concentrations when tested for antiviral activity against MDCK cells and did not exhibit antimicrobial activity against various

  通过各种靛红衍生物与N4取代的3-氨基硫脲缩合，再用苯甲酰溴环化产物，合成了一系列靛红-β-氨基硫脲和靛红-β-肼基噻唑啉。当测试对 MDCK 细胞的抗病毒活性时，该产品在较低浓度下表现出高毒性，并且对各种微生物没有表现出抗菌活性。
• Phenotypic and <i>in silico</i> studies for a series of synthetic thiosemicarbazones as New Delhi metallo-beta-lactamase carbapenemase inhibitors
  作者：Jonatham Souza Moreira、Danilo Santana Galvão、Carolina Ferreira Cavalcanti Xavier、Silvio Cunha、Samuel Silva da Rocha Pita、Joice Neves Reis、Humberto Fonseca de Freitas

  DOI：10.1080/07391102.2021.2001379

  日期：2022.12.26

  Inhibitory Concentration (FIC) ≤ 250 µM in the presence of meropenem (4 µg/mL). The most promising compound (FIC= 31.25 µM) also presented synergistic effect (FICI = 0.34). Docking and molecular dynamics studies on NDM-thiosemicarbazone complex suggested that 2,3-dihydro-1H-indol-2-one subunit interacts with catalytic zinc and interacted through hydrogen bonds with Asp124 acting like a carboxylic acid bioisostere

  摘要 过去二十年的特点是细菌对 β-内酰胺类药物产生耐药性，而碳青霉烯类衍生物是对抗多重耐药细菌的最终治疗方法。β-内酰胺酶表达与耐药性有关，这需要开发细菌耐药性阻断剂。丝氨酸-β-内酰胺酶和 β-内酰胺的药物抑制剂组合已成功用于治疗，尽管它们对新德里金属-β-内酰胺酶 (NDM) 没有活性。到目前为止，很少有化合物对产生 NDM 的细菌具有活性，也没有可用的特异性抑制剂。NDM抑制剂开发的合理策略从体外开始旨在寻找可以与 β-内酰胺抗生素协同作用的化合物的分析。因此，合成了八种缩氨基硫脲衍生物，并研究了它们逆转阴沟肠杆菌NDM 耐药表型的能力。 表型筛选表明，在美罗培南 (4 µg/mL) 存在的情况下，四种靛红-β-氨基硫脲显示分数抑制浓度 (FIC) ≤ 250 µM。最有前途的化合物 (FIC = 31.25 µM) 也呈现协同效应 (FICI = 0.34)。NDM-缩氨基硫脲络合物的对接和分子动力学研究表明，2
• Synthesis and Structure–Activity Evaluation of Isatin-β-thiosemicarbazones with Improved Selective Activity toward Multidrug-Resistant Cells Expressing P-Glycoprotein
  作者：Matthew D. Hall、Kyle R. Brimacombe、Matthew S. Varonka、Kristen M. Pluchino、Julie K. Monda、Jiayang Li、Martin J. Walsh、Matthew B. Boxer、Timothy H. Warren、Henry M. Fales、Michael M. Gottesman

  DOI：10.1021/jm2006047

  日期：2011.8.25

  Cancer multidrug resistance (MDR) mediated by ATP-binding cassette (ABC) transporters presents a significant unresolved clinical challenge. One strategy to resolve MDR is to develop compounds that selectively kill cells overexpressing the efflux transporter P-glycoprotein (MDR1, P-gp, ABCB1). We have previously reported structure-activity studies based around the lead compound NSC73306 (1, 1-isatin-4-(4'-methoxyphenyl)-3-thiosemicarbazone, 4.3-fold selective). Here we sought to extend this work on MDR1-selective analogues by establishing whether 1 showed "robust" activity against a range of cell lines expressing P-gp. We further aimed to synthesize and test analogues with varied substitution at the N4-position, and substitution around the N4-phenyl ring of isatin-beta-thiosemicarbazones (IBTs), to identify compounds with increased MDR1-selectivity. Compound 1 demonstrated MDR1-selectivity against all P-gp-expressing cell lines examined. This selectivity was reversed by inhibitors of P-gp ATPase activity. Structural variation at the 4'-phenyl position of 1 yielded compounds of greater MDR1-selectivity. Two of these analogues, 1-isatin-4-(4'-nitrophenyl)-3-thiosemicarbazone (22, 8.3-fold selective) and 1-isatin-4-(4'-tert-butyl phenyl)-3-thiosemicarbazone (32, 14.8-fold selective), were selected for further testing and were found to retain the activity profile of 1. These compounds are the most active IBTs identified to date.
• Synthesis and Preliminary CNS Depressant Activity Evaluation of New 3-[(3-Substituted-5-methyl-4-thiazolidinon-2-ylidene)hydrazono]-1H-2-indolinones and 3-[(2-Thioxo-3-substituted-4,5-imidazolidine-dion-1-yl)imino] - 1H-2-indolinones
  作者：Nilgün Karalí、Aysel Gürsoy、Nalan Terzioglu、Sumru Özkírímlí、Hülya Özer、Ahmet Cevdet Ekinci

  DOI：10.1002/(sici)1521-4184(199807)331:7/8<254::aid-ardp254>3.0.co;2-r

  日期：1998.7

  A series of (+/-) 3-[(3-substituted-5-methyl-4-thiazolidinon-2- ylidene)hydrazono]-1H-2-indolinones (2a-h) and 3-[(2-thioxo-3-substituted-4,5-imidazolidinedion-1-yl)imino] -1H-2-indolinones (3a-g) were synthesized by the cyclization of 3-(4-substituted-thiosemicarbazono)-1H-2-indolinones (1a-h) with ethyl 2-bromopropionate in anydrous ethanolic medium and oxalyl chloride in anhydrous diethyl ether, respectively. The structures of 2 and 3 were confirmed by analytical and spectral data (IR, 1H NMR, 13C NMR, and EIMS). The configuration of 3 was assigned on the basis of 1H NMR and 13C NMR data. 2c, 2d, 2g, 2h, and 3a-g were evaluated for anticonvulsant activity against maximal electroshock (MES) and subcutaneous pentylenetetrazol (ScMet) induced seizures. Among the compounds tested, only 2d exhibited some activity in anticonvulsant identification (Phase I) trials in mice. 2a, 2b, 2d, 2g, 2h, and 3a-g were additionally tested for potentiating effects on pentobarbital induced hypnosis in mice. All of the test compounds increased the sleeping time of pentobarbital significantly (p < 0.05) and the most potent compound was found to be 3a.
• Karali; Terzioglu; Guersoy, Bollettino Chimico Farmaceutico, 1998, vol. 137, # 3, p. 63 - 68
  作者：Karali、Terzioglu、Guersoy、Oetuek、Kiraz、Yegenoglu

  DOI：——

  日期：——