4-(3,4,5-三甲氧基苯基)-3-氨基硫脲 | 206762-46-1

• 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-(3,4,5-三甲氧基苯基)-3-氨基硫脲
• 英文名称: 4-(3',4',5'-trimethoxyphenyl)-3-thiosemicarbazide
• 英文别名: n-(3,4,5-Trimethoxyphenyl)hydrazinecarbothioamide；1-amino-3-(3,4,5-trimethoxyphenyl)thiourea
• CAS: 206762-46-1
• 化学式: C₁₀H₁₅N₃O₃S
• mdl: MFCD00060574
• 分子量: 257.313
• InChiKey: XNRLYRGZEKWEMJ-UHFFFAOYSA-N

物化性质

• 熔点：
  178 °C
• 沸点：
  373.9±52.0 °C(Predicted)
• 密度：
  1.297±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  110
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  4-(3,4,5-三甲氧基苯基)-3-氨基硫脲 、 靛红 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 以79%的产率得到(Z)-2-(2-oxoindolin-3-ylidene)-N-(3,4,5-trimethoxyphenyl)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
• 作为产物：
  描述：

  3,4,5-三甲氧基异硫氰酸苯酯 在 一水合肼 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 4-(3,4,5-三甲氧基苯基)-3-氨基硫脲
  参考文献：
  名称：

  新型缩氨基硫脲衍生物的合成作为抗糖尿病药物的酶动力学研究和抗氧化活性

  摘要：

  摘要 通过相应的氨基硫脲和 4-(甲基磺酰基)苯乙酮之间的缩合反应合成了新型氨基硫脲衍生物。所有化合物的化学结构均通过红外 (IR)、1 H-NMR 和13 C-NMR 光谱和质谱法阐明。所有化合物的抗氧化研究均使用 CUPRAC、FRAP、DPPH 方法进行。2-{1-[4-(Methylsulfonyl)phenyl]ethylidene} -N -phenylhydrazinecarbothioamide ( 1 ) 具有良好的抗氧化活性，SC 50值为 15.70 µM，也高于标准药物抗坏血酸。评估了所有化合物作为 α-糖苷酶和 α-淀粉酶抑制剂的抗糖尿病特性。发现化合物1是对 α-葡萄糖苷酶和 α-淀粉酶最具活性的化合物，IC 50值分别为 1.58 µM 和 3.24 µM。酶动力学研究表明化合物1具有竞争性结合模式。此外，分子对接研究通过检测化合物1与这些酶之间的分子相互作用，阐明了分子水平的结合机制。

  DOI：

  10.1080/10426507.2022.2099857

文献信息

• [EN] USE OF DERIVATIVES OF 2, 4-DIHYDRO-[1,2,4]TRIAZOLE-3-THIONE AS INHIBITORS O FTEH ENZYME MYELOPEROXIDASE (MPO)<br/>[FR] UTILISATION DE DERIVES DE 2, 4-DIHYDRO-[1,2,4]TRIAZOLE-3-THIONES COMME INHIBITEURS DE L'ENZYME MYELOPEROXYDASE (MPO)
  申请人：ASTRAZENECA AB

  公开号：WO2004096781A1

  公开（公告）日：2004-11-11

  There is disclosed the use of a compound of formula (I) wherein X, Y, W and Q are as defined in the specification, and pharmaceutically acceptable salts thereof, in the manufacture of a medicament, for the treatment or prophylaxis of diseases or conditions in which inhibition of the enzyme myeloperoxidase (MPO) is beneficial. Certain novel compounds of formula (I) and pharmaceutically acceptable salts thereof are disclosed, together with processes for their preparation. The compounds of formulae (I) are MPO inhibitors and are thereby particularly useful in the treatment or prophylaxis of neuroinflammatory disorders.

  揭示了使用公式(I)中X、Y、W和Q如规范中定义的化合物及其药用盐，在制造药物中用于治疗或预防对髓过氧化物酶（MPO）抑制有益的疾病或症状。公开了某些公式(I)的新化合物及其药用盐，以及它们的制备方法。公式(I)的化合物是MPO抑制剂，因此在治疗或预防神经炎症性疾病中特别有用。
• [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。
• Use of derivatives of 2, 4-dihydro-[1,2,4] triazole-3-thione as inhibitors of the enzyme myeloperoxidase (mpo)
  申请人：Svensson Mats

  公开号：US20070093483A1

  公开（公告）日：2007-04-26

  There is disclosed the use of a compound of formula (I) wherein X, Y, W and Q are as defined in the specification, and pharmaceutically acceptable salts thereof, in the manufacture of a medicament, for the treatment or prophylaxis of diseases or conditions in which inhibition of the enzyme myeloperoxidase (MPO) is beneficial. Certain novel compounds of formula (I) and pharmaceutically acceptable salts thereof are disclosed, together with processes for their preparation. The compounds of formulae (I) are MPO inhibitors and are thereby particularly useful in the treatment or prophylaxis of neuroinflammatory disorders.

  本发明揭示了使用化合物(I)的使用，其中X、Y、W和Q如规范中所定义，以及其药学上可接受的盐，在制造药物方面，用于治疗或预防抑制髓过氧化物酶（MPO）酶有益的疾病或状况。揭示了某些新型化合物(I)及其药学上可接受的盐，以及其制备方法。化合物(I)的MPO抑制剂，因此特别适用于治疗或预防神经炎症性疾病。
• USE OF DERIVATIVES OF 2, 4-DIHYDRO- 1,2,4 TRIAZOLE-3-THIONE AS INHIBITORS OF THE ENZYME MYELOPEROXIDASE (MPO)
  申请人：AstraZeneca AB

  公开号：EP1620410A1

  公开（公告）日：2006-02-01
• COMPOUNDS WITH MDR1-INVERSE ACTIVITY
  申请人：The Government of the United States of America as represented by the Secretary of the Department of Health and Human Services

  公开号：EP2240175A2

  公开（公告）日：2010-10-20