3-(p-chlorophenyl)-2-thiohydantoin | 55327-43-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 3-(p-chlorophenyl)-2-thiohydantoin
• 英文别名: 1-p-chlorophenyl-2-thiohadantoin；3-(4-chlorophenyl)-2-thioxoimidazolidin-4-one；3-(4-Chlor-phenyl)-2-thioxo-imidazolidin-4-on；1-(4-chlorophenyl)-2-sulfanyl-4,5-dihydro-1H-imidazol-5-one；3-(4-chlorophenyl)-2-sulfanylideneimidazolidin-4-one
• CAS: 55327-43-0
• 化学式: C₉H₇ClN₂OS
• mdl: MFCD06655458
• 分子量: 226.686
• InChiKey: GIKZSOCWOZJBCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  64.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(p-chlorophenyl)-2-thiohydantoin 在 sodium acetate 、 sodium hydride 作用下， 以 溶剂黄146 、 乙腈 为溶剂， 反应 16.5h， 生成 [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[(4Z)-1-(4-chlorophenyl)-4-[[4-(dimethylamino)phenyl]methylidene]-5-oxoimidazol-2-yl]sulfanyloxan-2-yl]methyl acetate
  参考文献：
  名称：

  2-硫代乙内酰脲衍生物的糖基化。一些新型的S-烷基化和S-葡萄糖基化乙内酰脲的合成

  摘要：

  3-芳基-5-（（Z）-亚芳基）-3-芳基-2-（2-甲基硫乙基）-2-硫代乙内酰脲3a-f和3-芳基-5-（（Z）-亚芳基）-2-（由3-芳基-5-（（Z）-亚芳基）的反应制备2'，3'，4'，6'-四-O-乙酰基-β-D-吡喃葡萄糖基）-2-硫代乙内酰脲7a-n。通过三种不同的途径，通过甲基硫代乙基氯或2'，3'，4'，6'-四-O-乙酰基-α-D-吡喃葡萄糖基溴与-2-巯基乙内酰脲2a-n结合。该化合物没有显示任何抗病毒和抗肿瘤活性。

  DOI：

  10.1016/s0008-6215(01)00040-4
• 作为产物：
  描述：

  N-(4-氯苯基)-2-氯乙酰胺 在 乙醇 、 氨 、 水 、 mercury dichloride 作用下， 生成 3-(p-chlorophenyl)-2-thiohydantoin
  参考文献：
  名称：

  Hill; Kelsey, Journal of the American Chemical Society, 1922, vol. 44, p. 2363

  摘要：

  DOI：

文献信息

• Design, synthesis, and anticancer evaluation of some novel thiourea, carbamimidothioic acid, oxazole, oxazolidine, and 2-amino-1-phenylpropyl-2-chloroacetate derived from L-norephedrine
  作者：Maged S. Abdel-Kader、Mostafa M. Ghorab、Mansour S. Alsaid、Saleh I. Alqasoumi

  DOI：10.1134/s1068162016040026

  日期：2016.7

  A novel series of thiourea, carbamimidothioic acid, 4, 5-dihydrooxazole-2-thiol, oxazolidine-2thine, and 2-amino-1-phenylpropyl-2-chloroacetate derivatives was designed and synthesized using 2-amino-1-phenylpropan-1-ol (L-norephedrine) as a strategic starting material. The structures of the newly synthesized compounds were established by elemental analyses, IR, and 1H NMR and 13C NMR spectral data

  使用 2-amino-1-phenylpropan-1 设计并合成了一系列新的硫脲、carbamimidothioic acid、4, 5-dihydrooxazole-2-thiol、oxazolidine-2thine 和 2-amino-1-phenylpropyl-2-chloroacetate 衍生物-ol（L-去甲麻黄碱）作为战略起始材料。新合成化合物的结构是通过元素分析、IR、1H NMR 和 13C NMR 光谱数据确定的。评估了这些化合物对各种癌细胞系的体外抗癌活性。相应的乙酰胺、氨基甲亚氨基硫酸和 2-2-氨基-1-苯基丙基-2-氯乙酸衍生物显示出与标准药物阿霉素对人乳腺癌细胞系 (MCF-7) 几乎相同的活性。还，
• Three types of copper derivatives formed by CuCl₂·2H₂O interaction with (<i>Z</i>)-3-aryl-2-(methylthio)-5-(pyridine-2-ylmethylene)-3,5-dihydro-4<i>H</i>-imidazol-4-ones
  作者：Dmitry Guk、Alexei Naumov、Olga Krasnovskaya、Viktor Tafeenko、Anna Moiseeeva、Vladimir Pergushov、Michail Melnikov、Nikolai Zyk、Alexander Majouga、Elena Belolglazkina

  DOI：10.1039/d0dt02817g

  日期：——

  presence of a reducing solvent (alcohol or dimethylformamide (DMF)) produce three types of Cu-containing compounds: two Cu complexes with a composition of CuII(3)Cl2 (4) and CuI(3)Cl (5) as well as a salt (3 + H)+CuICl2− (6) in a 4 : 5 : 6 ratio depending on the substituent at the N(3) nitrogen atom of the ligand moiety. In non-reducing solvents (dimethyl sulfoxide (DMSO) and CHCl3/acetone), only complexes

  （Z）-3-芳基-2-（甲硫基）-5-（吡啶-2-基亚甲基）-3,5-二氢-4 H-咪唑-4-酮（3）与CuCl 2 ·2H 2的反应O在还原溶剂（酒精或二甲基甲酰胺（DMF））存在下会产生三种类型的含Cu化合物：两种具有Cu II（3）Cl 2（4）和Cu I（3）Cl（5）以及盐（3 + H）+的Cu我氯2 - （6）在4  ： 5  ：  6的比例根据在N（3）的配体部分的氮原子上的取代基。在非还原性溶剂（二甲亚砜（DMSO）和CHCl 3 /丙酮），只配合物4形成，所有这三个铜衍生物（4，5，和6）通过单晶X射线衍射，UV / VIS进行了表征光谱学和电化学数据。记录了方便的电化学和紫外可见光谱标准，这使得区分不同的含铜化合物成为可能。根据电子光谱和电子顺磁共振（EPR）数据，可能形成化合物4-6的方案提出，包括铜（初始协调II）氯化物与有机配体，随后的还原所得到的复合物4通过用D
• Microwave‐Assisted Solid‐State Synthesis and Characterization of Thiohydantoin Derivatives
  作者：Jian‐Ping Li、Chun‐Ming Ma、Gui‐Rong Qu

  DOI：10.1081/scc-200054778

  日期：2005.5

  A new and efficient solid-state method for the preparation of thiohydantoins is reported. With this method, twelve thiohydantoin compounds have been synthesized in good to excellent yields (81-92%). In addition, this method has the advantages of high yields, a cleaner reaction, simple methodology, and short reaction times.
• Structural optimization of non-nucleoside DNA methyltransferase inhibitor as anti-cancer agent
  作者：Bo Zhong、Sergei Vatolin、Nethrie D. Idippily、Rati Lama、Laila A. Alhadad、Frederic J. Reu、Bin Su

  DOI：10.1016/j.bmcl.2016.01.020

  日期：2016.2

  Inhibition of DNA methyltransferase 1 (DNMT1) can reverse the malignant behavior of cancer cells by restoring expression of aberrantly silenced genes that are required for differentiation, senescence, and apoptosis. Clinically used DNMT1 inhibitors decitabine and azacitidine inhibit their target by covalent trapping after incorporation into DNA as azacytidine analogs. These nucleoside compounds are prone to rapid enzymatic inactivation in blood, posing challenges to the development of purely epigenetic dosing schedules. Non-nucleoside compounds that suppress expression or function of DNMT1 may overcome this problem. Using a high-throughput PCR-based site specific chromatin condensation assay, we identified a compound that reactivated Cyclin-Dependent Kinase Inhibitor 2A (CDKN2A) in myeloma cells and suppressed expression of DNMT1 from a library of 5120 chemically diverse small molecules. Lead optimization was performed to generate 26 new analogs with lung cancer proliferation and DNMT1 expression as activity readout. Two of the new derivatives showed 2 fold improvement of growth inhibiting potency and also decreased DNMT1 protein levels in lung cancer cells. Published by Elsevier Ltd.
• Dains; Thompson; Asendorf, Journal of the American Chemical Society, 1922, vol. 44, p. 2313
  作者：Dains、Thompson、Asendorf

  DOI：——

  日期：——