(Z)-N-cyclohexyl-2-(2-oxoindolin-3-ylidene)hydrazinecarbothioamide | 1318765-17-1

• 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: (Z)-N-cyclohexyl-2-(2-oxoindolin-3-ylidene)hydrazinecarbothioamide
• CAS: 1318765-17-1；92460-98-5
• 化学式: C₁₅H₁₈N₄OS
• 分子量: 302.4
• InChiKey: HTNHFARNIZWIGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.14
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  65.52
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  N-[[(cyclohexylamino)-sulfanylidenemethyl]amino]carbamic acid tert-butyl ester 在 盐酸 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 生成 (Z)-N-cyclohexyl-2-(2-oxoindolin-3-ylidene)hydrazinecarbothioamide
  参考文献：
  名称：

  Synthesis and Structure–Activity Evaluation of Isatin-β-thiosemicarbazones with Improved Selective Activity toward Multidrug-Resistant Cells Expressing P-Glycoprotein

  摘要：

  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.

  DOI：

  10.1021/jm2006047

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。
• [EN] THIOSEMICARBAZONES WITH MDR1 - INVERSE ACTIVITY<br/>[FR] THIOSEMICARBAZONES À ACTIVITÉ ANTI-MDR1
  申请人：US HEALTH

  公开号：WO2012033601A1

  公开（公告）日：2012-03-15

  Disclosed herein are drug compounds that have MDR-inverse activity and thus are effective against multidrug-resistant cells. Exemplary compounds disclosed herein have the structure;Formula (I). Examples of the disclosed compounds have been found to have, inter alia, efficacy in directly treating multidrug resistant cells, rendering multidrug resistant cells susceptible to other chemotherapeutics and in some instances reversing multidrug resistance.

  本文披露了具有MDR逆转活性的药物化合物，因此对多药耐药细胞有效。本文披露的示例化合物具有下列结构；公式（I）。已发现披露的化合物的示例具有直接治疗多药耐药细胞的功效，使多药耐药细胞对其他化疗药物敏感，并在某些情况下逆转多药耐药。
• Solvatochromism and Optoelectronic Properties of Thiosemicarbazone Derivatives Having π-Conjugated Systems
  作者：Yunus Emre Kara、Yadigar Gülseven Sıdır、İsa Sıdır、Fatma Kandemirli

  DOI：10.1007/s10953-023-01248-5

  日期：——

  properties of thiosemicarbazone derivatives having five different π-conjuged systems have been investigated. UV–Vis absorption spectra of TSC (Thiosemicarbazone) derivatives have been measured in 18 solvent media with different polarities. The global electronic transition in these compounds is described as π−π* electronic transition resulting from the resonance in the thiosemicarbazone group. The other

  研究了具有五种不同π共轭系统的缩氨基硫脲衍生物的电子结构、溶剂化显色和 LSER（线性溶剂化能量关系）性质。已在 18 种不同极性的溶剂介质中测量了 TSC（缩氨基硫脲）衍生物的 UV-Vis 吸收光谱。这些化合物中的全局电子跃迁被描述为π − π * 电子跃迁，由缩氨基硫脲基团的共振引起。其他较低波长的最大值表示为吲哚环中的π − π * 电子跃迁和n − π* 羧基中的电子跃迁。为了确定全局电子跃迁的分析溶剂-溶质相互作用，已经使用 LSER 以及 Kamlet-Taft 和 Catalán 参数进行了研究。已经生成了具有 Reichardt 参数和 Marcus 溶剂函数的电子跃迁波数之间的溶剂化变色模型。已经使用 Moss、Ravindra、Herve-Vándamme、Kumar、Singh 和 Reddy 关系研究了光电特性。根据E g（分子能隙）值，所研究的化合物可以被认为是有机半导体材料。
• Insight on a new indolinone derivative as an orally bioavailable lead compound against renal cell carcinoma
  作者：Marwa A. Fouad、Mayssoune Y. Zaki、Raghda A. Lotfy、Walaa R. Mahmoud

  DOI：10.1016/j.bioorg.2021.104985

  日期：2021.7
• Karali; Gursoy, Il Farmaco, 1994, vol. 49, # 12, p. 819 - 822
  作者：Karali、Gursoy

  DOI：——

  日期：——