4-(2,5-二氯苯基)-3-氨基硫脲 | 61335-34-0

• 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-(2,5-二氯苯基)-3-氨基硫脲
• 英文名称: 4-(2,5-dichlorophenyl)-3-thiosemicarbazide
• 英文别名: 4-(2,5-dichloro-phenyl)-thiosemicarbazide；1-amino-3-(2,5-dichlorophenyl)thiourea
• CAS: 61335-34-0
• 化学式: C₇H₇Cl₂N₃S
• 分子量: 236.125
• InChiKey: XBDSQQOEXKOZJQ-UHFFFAOYSA-N

物化性质

• 熔点：
  62 °C(Solv: ethanol (64-17-5))
• 沸点：
  336.3±52.0 °C(Predicted)
• 密度：
  1.571±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  二硫化碳 、 4-(2,5-二氯苯基)-3-氨基硫脲 以 乙醇 为溶剂， 生成 5-(2,5-dichloro-anilino)-3H-[1,3,4]thiadiazole-2-thione
  参考文献：
  名称：

  Wahab, Bollettino Chimico Farmaceutico, 1979, vol. 118, # 7, p. 391 - 396

  摘要：

  DOI：
• 作为产物：
  描述：

  2,5-二氯异硫氰酸苯酯 在 一水合肼 作用下， 以 异丙醇 为溶剂， 反应 3.0h， 以79%的产率得到4-(2,5-二氯苯基)-3-氨基硫脲
  参考文献：
  名称：

  硫代氨基脲，具​​有有前景的吲哚胺-2,3-双加氧酶（IDO）抑制特性的片段

  摘要：

  为了探索硫代氨基脲化合物对抑制吲哚胺2,3-二加氧酶（IDO）的兴趣，IDA是抗癌免疫疗法的有希望的治疗靶标，制备了一系列32种苯基硫代氨基脲衍生物并评估了它们对IDO的抑制作用。我们的研究表明，在这些衍生物中，在硫代氨基脲上具有4-氰基苯基特征的化合物14是该系列中最有效的IDO抑制剂，具有IC 50为1.2μM。所描绘的SAR显示，相对于苯硫代氨基脲而言，在3-位和4-位的取代非常有前景，而在2-位的取代总是导致效力较低或无活性的衍生物。实际上，该研究突出了一种新颖有趣的IDO抑制支架，以进一步发展。

  DOI：

  10.1016/j.ejmech.2014.05.044

文献信息

• Thiosemicarbazide, a fragment with promising indolamine-2,3-dioxygenase (IDO) inhibition properties
  作者：Silvia Serra、Laurence Moineaux、Christelle Vancraeynest、Bernard Masereel、Johan Wouters、Lionel Pochet、Raphaël Frédérick

  DOI：10.1016/j.ejmech.2014.05.044

  日期：2014.7

  of the indoleamine 2,3-dioxygenase (IDO), a promising therapeutic target for anticancer immunotherapy, a series of 32 phenylthiosemicarbazide derivatives was prepared and their IDO inhibition evaluated. Our study demonstrated that among these derivatives, compound 14 characterized with a 4-cyanophenyl group on the thiosemicarbazide was the more potent IDO inhibitor in this series being endowed with an

  为了探索硫代氨基脲化合物对抑制吲哚胺2,3-二加氧酶（IDO）的兴趣，IDA是抗癌免疫疗法的有希望的治疗靶标，制备了一系列32种苯基硫代氨基脲衍生物并评估了它们对IDO的抑制作用。我们的研究表明，在这些衍生物中，在硫代氨基脲上具有4-氰基苯基特征的化合物14是该系列中最有效的IDO抑制剂，具有IC 50为1.2μM。所描绘的SAR显示，相对于苯硫代氨基脲而言，在3-位和4-位的取代非常有前景，而在2-位的取代总是导致效力较低或无活性的衍生物。实际上，该研究突出了一种新颖有趣的IDO抑制支架，以进一步发展。
• Me₃N-promoted synthesis of 2,3,4,4a-tetrahydroxanthen-1-one: preparation of thiosemicarbazone derivatives, their solid state self-assembly and antimicrobial properties
  作者：Aminah Hameed、Zahid Shafiq、Muhammad Yaqub、Mazhar Hussain、Muhammad Ajaz Hussain、Muhammad Afzal、Muhammad Nawaz Tahir、Muhammad Moazzam Naseer

  DOI：10.1039/c5nj01879j

  日期：——

  Thiosemicarbazones (5a–5j) have been synthesized from 2,3,4,4a-tetrahydroxanthen-1-one, obtained in high yield through Me₃N-promoted domino Baylis–Hillman/oxa-Michael reaction. Their solid-state self-assembly and antimicrobial properties are studied.

  硫代半卡巴松（5a-5j）已从2,3,4,4a-四羟基蒽醌-1-酮合成，该化合物通过Me₃N催化的多米诺贝利斯-希尔曼/氧-迈克尔反应获得高收率。研究了它们的固态自组装和抗菌性能。

• Synthesis and Biological Evaluation of Some New N4-Aryl Substituted 5-Chloroisatin-3-thiosemicarbazones
  作者：Humayun Pervez、Muhammad Ramzan、Muhammad Yaqub、Faiz-ul-Hassan Nasim、Khalid Mohammed Khan

  DOI：10.2174/1573406411208030505

  日期：2012.5.1

  A new series of sixteen N4-aryl substituted 5-chloroisatin-3-thiosemicarbazones 2a-2p has been synthesized, characterized and tested for selected biological activities i.e. cytotoxicity, phytotoxicity and urease inhibition. In the brine shrimp bioassay, all the synthesized compounds gave LD50 values 2.30 X 10-4 M - 2.79 X 10-4 M and were, therefore, found to be almost inactive, whereas in phytotoxicity assay, regardless of the nature of aryl substituents, they displayed weak to moderate (5-40%) phytotoxic activity at the highest tested concentrations (500 or 1000 μg/mL). In urease inhibition bioassay, compounds 2a, 2c, 2e, 2f, 2k and 2m exhibited relatively a higher degree of urease inhibition with IC50 values ranging from 38.91 μM to 76.65 μM and thus proved to be potent inhibitors of the enzyme. Of these, 2f and 2m displayed pronounced inhibition with IC50 values 38.91 μM and 39.50 μM, respectively, and may act as lead compounds for further studies. Structure-activity relationship (SAR) studies revealed that electronic effects of the substituents about the phenyl ring at N4 of the thiosemicarbazone moiety played an important role in enhancing the urease inhibitory potential of some of the synthesized compounds.

  合成了一系列16种N4-芳基取代的5-氯靛红-3-缩氨基硫脲2a-2p，并对它们进行了表征和选择性生物活性测试，包括细胞毒性、植物毒性和脲酶抑制活性。在卤虫生物测定中，所有合成化合物的LD50值为2.30 X 10-4 M至2.79 X 10-4 M，因此被发现几乎无活性；而在植物毒性测定中，无论芳基取代基的性质如何，它们在最高测试浓度（500或1000 μg/mL）下表现出微弱至中等的（5-40%）植物毒性活性。在脲酶抑制生物测定中，化合物2a、2c、2e、2f、2k和2m表现出较高的脲酶抑制程度，IC50值范围为38.91 μM至76.65 μM，证明了它们是该酶的有效抑制剂。其中，2f和2m表现出显著的抑制作用，IC50值分别为38.91 μM和39.50 μM，可能作为进一步研究的先导化合物。结构-活性关系（SAR）研究表明，缩氨基硫脲部分N4位苯环上的取代基的电子效应对某些合成化合物的脲酶抑制潜力起着重要作用。
• Synthesis, Cytotoxic and Phytotoxic Effects of Some New N4-Aryl Substituted Isatin-3-thiosemicarbazones
  作者：Humayun Pervez、Muhammad Ramzan、Muhammad Yaqub、Khalid Mohammed Khan

  DOI：10.2174/157018011795514159

  日期：2011.6.1

  A series of N4-aryl substituted isatin-3-thiosemicarbazones was prepared by the reaction of isatin with an appropriate thiosemicarbazide in ethanol containing a few drops of acetic acid. The newly synthesized compounds were characterized by means of their analytical (CHN) and spectral (IR, 1H-NMR, EIMS) data, and evaluated for their cytotoxicity and phytotoxicity potential. Eleven out of thirteen compounds tested proved to be active in the brine-shrimp lethality bioassay exhibiting significant cytotoxic activity with LD50 values ranging from 1.75x10-5M to 1.91x10-4M. In phytotoxicity assay, all the synthesized compounds, regardless of the nature of aryl substituents, demonstrated weak to moderate (5-30%) plant growth inhibition at the highest tested concentration (500 μg/mL).

  一系列N4-芳基取代的异吲哚-3-硫半卡巴脒通过异吲哚与适当的硫脲在含有几滴醋酸的乙醇中反应制备。新合成的化合物通过其分析（CHN）和谱学（IR、1H-NMR、EIMS）数据进行表征，并评估了它们的细胞毒性和植物毒性潜力。在十三种测试的化合物中，有十一种在卤虫 lethality 生物测定中表现出显著的细胞毒活性，LD50值范围从1.75x10-5M到1.91x10-4M。在植物毒性测定中，所有合成的化合物，无论芳基取代基的性质如何，在最高测试浓度（500 μg/mL）下均表现出轻微至中等（5-30%）的植物生长抑制作用。
• Design, Synthesis and Bioactivity of Novel Glycosylthiadiazole Derivatives
  作者：Guanghui Zong、Hanqing Zhao、Rui Jiang、Jianjun Zhang、Xiaomei Liang、Baoju Li、Yanxia Shi、Daoquan Wang

  DOI：10.3390/molecules19067832

  日期：——

  A series of novel glycosylthiadiazole derivatives, namely 2-phenylamino-5-glycosyl-1,3,4-thiadiazoles, were designed and synthesized by condensation between sugar aldehydes A/B and substituted thiosemicarbazide C followed by oxidative cyclization by treating with manganese dioxide. The original fungicidal activities results showed that some title compounds exhibited excellent fungicidal activities against Sclerotinia sclerotiorum (Lib.) de Bary and Pyricularia oryzae Cav, especially compounds F-5 and G-8 which displayed better fungicidal activities than the commercial fungicide chlorothalonil. At the same time, the preliminary studies based on the Elson-Morgan method indicated that many compounds exhibited some inhibitory activity toward glucosamine-6-phosphate synthase (GlmS). The structure-activity relationships (SAR) are discussed in terms of the effects of the substituents on both the benzene and the sugar ring.

  设计并合成了一系列新型糖基噻二唑衍生物，即2-苯胺基-5-糖基-1,3,4-噻二唑，通过糖醛A/B与取代硫脲C缩合反应，随后用二氧化锰氧化环化得到。初步的杀菌活性结果表明，某些目标化合物对核盘菌（Lib.) de Bary和稻瘟病菌Cav具有优异的杀菌活性，尤其是化合物F-5和G-8的杀菌活性优于商业杀菌剂百菌清。同时，基于Elson-Morgan法的初步研究表明，许多化合物对葡萄糖胺-6-磷酸合酶（GlmS）具有一定的抑制活性。根据苯环和糖环上的取代基对结构-活性关系（SAR）进行了讨论。