4-(4-叔丁基苯基)-氨基硫脲 | 109509-79-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-(4-叔丁基苯基)-氨基硫脲
• 英文名称: 4-(4-tert-Butyl-phenyl)-thiosemicarbazid
• 英文别名: 4-<4-tert-Butyl-phenyl>-thiosemicarbazid；4-(4'-tert-butylphenyl)-3-thiosemicarbazide；4-(4-tert-butyl-phenyl)-thiosemicarbazide；N-(4-tert-Butylphenyl)hydrazinecarbothioamide；1-amino-3-(4-tert-butylphenyl)thiourea
• CAS: 109509-79-7
• 化学式: C₁₁H₁₇N₃S
• 分子量: 223.342
• InChiKey: RLKQMJZDEMLBLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  82.2
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(4-叔丁基苯基)-氨基硫脲 在 盐酸 、 sodium nitrite 作用下， 生成 5-<4-tert-Butylanilino>-1.2.3.4-thiotriazol
  参考文献：
  名称：

  Dubenko,R.G. et al., Journal of general chemistry of the USSR, 1963, vol. 33, p. 266 - 268

  摘要：

  DOI：
• 作为产物：
  描述：

  4-叔丁基苯异硫氰酸酯 在 一水合肼 作用下， 以 四氢呋喃 为溶剂， 生成 4-(4-叔丁基苯基)-氨基硫脲
  参考文献：
  名称：

  发现具有有效和选择性抗光滑念珠菌活性的新型缩氨基硫脲衍生物

  摘要：

  摘要 基于我们内部化合物库筛选的命中化合物1 ，设计并合成了一系列包含缩氨基硫脲部分的 21 种新型化合物。大多数化合物在体外对七种常见病原真菌显示出有效的抗真菌活性。值得注意的是，所有化合物都显示出对光滑念珠菌537的高效力（MIC = ≤0.0156-2 µg/mL）。值得注意的是，化合物5j和5r对Candida krusei 4946 和Candida auris 922 表现出优异的抗真菌活性。此外，化合物5j和5r还对 15  C. glabrata表现出高效力分离物的 MIC 值范围为 0.0625 µg/mL 至 4 µg/mL，化合物5r略优于5j。此外，化合物5r对C. glabrata的生物膜形成有一定的抑制作用。此外，化合物5r对 HUVEC 的细胞毒性最小，IC 50值为 15.89 µg/mL，在 64 µg/mL 时无溶血作用。总之，这些结果表明有前途的先导化合物5r值得进一步研究。

  DOI：

  10.1080/14756366.2023.2202362

文献信息

• [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。
• 5‐Fluoro/(trifluoromethoxy)‐2‐indolinone derivatives with anti‐interleukin‐1 activity
  作者：Özge Soylu‐Eter、Zekiye Şeyma Sevinçli、Betül Ersoy、Bahar Hasanusta、Uğur Gatfar、Nathan A. Lack、Burak Erman、Ahmet Gül、Hakan S. Orer、Nilgün Karalı

  DOI：10.1002/ardp.202300217

  日期：2023.12

  2-indolinone derivatives in preliminary studies to develop agents with anti-IL-1 activity. First, the putative efficacies and binding interactions of 2-indolinones were evaluated by docking studies. Second, previously synthesized 5-fluoro/(trifluoromethoxy)−1H-indole-2,3-dione 3-(4-phenylthiosemicarbazones) (compounds 47–69) which had the highest inhibitory effect in the screening were evaluated for inhibitory

  促炎细胞因子白介素-1 (IL-1) 驱动多种炎症性疾病的发病机制。最近的研究表明，2-吲哚酮可以调节细胞因子反应。因此，我们在初步研究中筛选了几种2-二氢吲哚酮衍生物，以开发具有抗IL-1活性的药物。首先，通过对接研究评估了 2-吲哚酮的假定功效和结合相互作用。其次，评估了先前合成的在筛选中具有最高抑制效果的5-氟/(三氟甲氧基)−1 H-吲哚-2,3-二酮3-(4-苯硫代缩氨基脲)（化合物47-69 ）的抑制效果。 IL-1 受体 (IL-1R)。选择化合物52 (IC 50 = 0.09 µM) 和65 (IC 50 = 0.07 µM) 作为先导化合物，用于随后合成新衍生物。设计、合成了新型5-氟/(三氟甲氧基)−1 H-吲哚-2,3-二酮3-(4-苯硫代缩氨基脲)（化合物70-116 ），并完成了体外研究。测试的化合物76 、 78 、 81 、 91 、 100 、 105和107在
• 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.
• [EN] TRKA AS A TARGET FOR INHIBITING APP CLEAVAGE AND/OR PROGRESSION OF ALZHEIMER'S DISEASE<br/>[FR] TRKA COMME CIBLE POUR L'INHIBITION DU CLIVAGE D'APP ET/OU LA PROGRESSION DE LA MALADIE D'ALZHEIMER
  申请人：BUCK INST FOR RES ON AGING

  公开号：WO2013026021A2

  公开（公告）日：2013-02-21

  In various embodiments method are provided for inhibiting (partially or fully) the C-terminal cleavage of APP resulting in the formation of APP-C31 peptide and APPneo (APP664) in a mammal. The methods typically involve administering or causing to be administered to the mammal a TrkA kinase inhibitor in an amount sufficient to reduce C-terminal cleavage of APP and production of a C31 peptide and/or APPneo. In certain embodiments the inhibitor comprises ADDN-1351 or a derivative thereof.
• Dubenko,R.G. et al., Journal of general chemistry of the USSR, 1963, vol. 33, p. 266 - 268
  作者：Dubenko,R.G. et al.

  DOI：——

  日期：——