4-(2,4-dimethoxyphenyl)thiosemicarbazide | 122813-69-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(2,4-dimethoxyphenyl)thiosemicarbazide
• 英文别名: N-(2,4-dimethoxyphenyl)thiosemicarbazide；4-(2,4-dimethoxyphenyl)-3-thiosemicarbazide；1-Amino-3-(2,4-dimethoxyphenyl)thiourea
• CAS: 122813-69-8
• 化学式: C₉H₁₃N₃O₂S
• 分子量: 227.287
• InChiKey: UDUUIZZHXOZOLU-UHFFFAOYSA-N

物化性质

• 沸点：
  370.3±52.0 °C(Predicted)
• 密度：
  1.303±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  101
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(2,4-dimethoxyphenyl)thiosemicarbazide 在 水 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 生成 3-(2,4-dimethoxyanilino)-5-methyl-1H-pyrazole-4-carboxylic acid
  参考文献：
  名称：

  发现口服活性吡唑并喹啉作为有效的PDE10抑制剂可用于精神分裂症的治疗

  摘要：

  已合成了一系列吡唑并喹啉类似物，并显示出与PDE10的高亲和力结合。通过SAR研究和我们的前导优化工作，发现化合物16和27在MK-801诱导的多动症大鼠模型中具有有效的口服抗精神病活性。

  DOI：

  10.1016/j.bmcl.2011.11.023
• 作为产物：
  描述：

  potassium (2,4-dimethoxyphenyl)carbamodithioate 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 4-(2,4-dimethoxyphenyl)thiosemicarbazide
  参考文献：
  名称：

  5-Nitrofuran-2-yl derivatives: Synthesis and inhibitory activities against growing and dormant mycobacterium species

  摘要：

  Eighteen 5-nitrofuran-2-yl derivatives were prepared by reacting 5-nitro-2-furfural with various (sub)phenyl/pyridyl thiosemicarbazide using microwave irradiation. The compounds were tested for their in vitro activity against tubercular and various non-tubercular mycobacterium species in log-phase and 6-week-starved cultures. Compound N-(3,5-dibromopyridin-2-yl)-2-((5-nitrofuran-2-yl) methylene) hydrazinecarbothioamide (4r) was found to be the most potent compound (MIC: 0.22 mu M) and was 3 times more active than standard isoniazid (INH) and equally active as rifampicin (RIF) in log-phase culture of Mycobacterium tuberculosis H37Rv. In starved M. tuberculosis H37Rv, 4r inhibited with MIC of 13.9 mu M and was found to be 50 times more active than INH and slightly more active than RIF. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.12.088

文献信息

• 3-amino-5-methyl-1H-pyrazole-4-carboxylic acids and esters thereof as
  申请人：A. H. Robins Company, Incorporated

  公开号：US04826866A1

  公开（公告）日：1989-05-02

  A novel method of controlling epilepsy, muscle tension, muscular spasticity, and anxiety in living animal bodies by administering compounds of the formula: ##STR1## wherein: R.sup.1 is hydrogen, loweralkyl or a pharmaceutically acceptable cation; R.sup.2 and R.sup.3, same or different, are hydrogen, loweralkyl, aryl, cycloalkyl, loweralkenyl, 1-adamantyl, heterocyclicaminoalkyl, diloweralkylaminoloweralkyl, or R.sup.2 with R.sup.3 and adjacent nitrogen may form a heterocyclic ring structure; and the pharmaceutical acceptable acid salts, and tautomeric isomers thereof; and novel pharmaceutical compositions therefor are disclosed.

  一种通过给予以下式化合物来控制癫痫、肌肉紧张、肌肉痉挛和焦虑的新方法，其中：##STR1## 其中：R.sup.1 为氢、较低的烷基或药学上可接受的阳离子；R.sup.2 和 R.sup.3，相同或不同，为氢、较低的烷基、芳基、环烷基、较低的烯基、1-金刚烷基、杂环氨基烷基、二较低烷基氨基较低烷基，或 R.sup.2 与 R.sup.3 和相邻的氮原子可能形成杂环环结构；以及其药学上可接受的酸盐和互变异构体；以及相关的新型药物组合物。
• 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。
• Synthesis and Toxicity Evaluation of Some N4-Aryl Substituted 5-Trifluoromethoxyisatin-3-thiosemicarbazones
  作者：Humayun Pervez、Naveeda Saira、Mohammad Saeed Iqbal、Muhammad Yaqub、Khalid Mohammed Khan

  DOI：10.3390/molecules16086408

  日期：——

  A series of twenty one N4-aryl substituted 5-trifluoromethoxyisatin-3-thiosemicarbazones 3a-3u was synthesized by the reaction of trifluoromethoxyisatin 1 with different arylthiosemicarbazides 2 in aqueous ethanol (50%), containing a few drops of acetic acid. Their structures were established on the basis of analytical (CHN) and spectral (IR, 1H-NMR, EIMS) data. All the synthesized compounds were evaluated for their toxicity potential by a brine shrimp lethality bioassay. Ten compounds i.e., 3a, 3e, 3i-3l and 3n-3q proved to be active in this assay, displaying promising toxicity (LD50 = 1.11 × 10−5 M − 1.80 × 10−4 M). Amongst these, 3k, 3n and 3o were found to be the most active ones (LD50 = 1.11 × 10−5 M − 1.43 × 10−5 M). Compound 3k showed the highest activity with a LD50 value of 1.11 × 10−5 M and can, therefore, be used as a lead for further studies. Structure-activity relationship (SAR) studies revealed that the presence of strong inductively electron-attracting trifluoromethoxy substituent at position-5 of the isatin moiety played an important role in inducing or enhancing toxic potentiality of some of the synthesized compounds.

  通过三氟甲氧基异吲哚1与不同芳基缩氨基脲2在含有几滴醋酸的50%乙醇水溶液中的反应，合成了一系列21种N4-芳基取代的5-三氟甲氧基异吲哚-3-缩氨基脲3a-3u。它们的结构是基于分析（CHN）和光谱（IR，1H-NMR，EIMS）数据确定的。所有合成的化合物都通过卤虫致死生物测定法评估了它们的毒性潜力。其中10种化合物，即3a，3e，3i-3l和3n-3q在此测定中表现活跃，显示出有前景的毒性（LD50 = 1.11 × 10−5 M − 1.80 × 10−4 M）。在这些化合物中，3k，3n和3o被发现是最活跃的（LD50 = 1.11 × 10−5 M − 1.43 × 10−5 M）。化合物3k显示出最高的活性，其LD50值为1.11 × 10−5 M，因此可以作为进一步研究的先导化合物。构效关系（SAR）研究表明，在异吲哚部分的5位上存在强诱导电子吸引的三氟甲氧基取代基，在诱导或增强某些合成化合物的毒性潜力方面发挥了重要作用。
• Synthesis of substituted 3-(5-amino-[1,3,4]thiadiazol-2-yl)-2<i>H</i>-pyrano[2,3-<i>c</i>]pyridin-2-ones
  作者：Irina O. Zhuravel'、Sergiy M. Kovalenko、Alexandre V. Ivachtchenko、Valentin P. Chernykh、Pavlo E. Shinkarenko

  DOI：10.1002/jhet.5570410407

  日期：2004.7

  An efficient two-step synthesis of novel 3-(5-amino-[1,3,4]thiadiazol-2-yl)-2H-pyrano[2,3-c]pyridine-2-ones was developed. In the first step, a new 2H-pyrano[2,3-c]pyridine-3-carboxamide 5 was prepared by Knoevenagel condensation of pyridoxal hydrochloride with cyanoacetamide. In the second step, the reaction of carboxamide 5 with a series of N4-substituted thiosemicarbazides yielded a library of 35

  开发了有效的两步合成新型3-（5-氨基-[1,3,4]噻二唑-2-基）-2 H-吡喃并[2,3 - c ]吡啶-2-酮。第一步，通过吡pyr醛盐酸盐与氰基乙酰胺的Knoevenagel缩合制备新的2 H-吡喃并[2,3 - c ]吡啶-3-甲酰胺5。在第二步中，羧酰胺5与一系列N 4取代的硫代氨基脲的反应以高收率产生了35种离散化合物8 1-35}的库。讨论了导致这些产物的分子间再循环机理。