N-(4-乙氧基苯基)肼硫代甲酰胺 | 64374-52-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: N-(4-乙氧基苯基)肼硫代甲酰胺
• 英文名称: 4-(p-ethoxyphenyl)thiosemicarbazide
• 英文别名: p-ethoxyphenyl thiosemicarbazide；4-(p-Ethoxy-phenyl)-thiosemicarbazid；-thiosemicarbazid；4-<4-Ethoxy-phenyl>-thiosemicarbazid；4-(4-ethoxy-phenyl)-thiosemicarbazide；4-(4-Aethoxy-phenyl)-thiosemicarbazid；1-amino-3-(4-ethoxyphenyl)thiourea
• CAS: 64374-52-3
• 化学式: C₉H₁₃N₃OS
• mdl: MFCD00060583
• 分子量: 211.288
• InChiKey: COOLKSFDRDWEMC-UHFFFAOYSA-N

物化性质

• 熔点：
  149-150 °C
• 沸点：
  343.0±44.0 °C(Predicted)
• 密度：
  1.266±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  91.4
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  N-(4-乙氧基苯基)肼硫代甲酰胺 在 碳酸二乙酯 作用下， 以 乙二醇甲醚 为溶剂， 反应 4.0h， 生成 N,N'-bis-(4-ethoxy-phenyl)-[1,3,4]thiadiazole-2,5-diamine
  参考文献：
  名称：

  Reaction of Diethyl Carbonate with 4-Substituted Thiosemicarbazides

  摘要：

  DOI：

  10.1021/jo01070a511
• 作为产物：
  描述：

  4-乙氧基苯基硫氰酸酯 在 肼 作用下， 生成 N-(4-乙氧基苯基)肼硫代甲酰胺
  参考文献：
  名称：

  Buu-Hoi et al., Journal of the Chemical Society, 1956, p. 2160,2161

  摘要：

  DOI：

文献信息

• Synthesis, Anticancer and Antibacterial Activity of Some Novel Mononuclear Ru(II) Complexes
  作者：Upal Kanti Mazumder、Malaya Gupta、Subhas Somalingappa Karki、Shiladitya Bhattacharya、Suresh Rathinasamy、Sivakumar Thangavel

  DOI：10.1248/cpb.52.178

  日期：——

  In search of potential anticancer drug candidates in ruthenium complexes, a series of mononuclear ruthenium complexes of the type [Ru(phen)2(nmit)]Cl2 (Ru1), [Ru(bpy)2(nmit)]Cl2 (Ru2), [Ru(phen)2(icpl)]Cl2 (Ru3), Ru(bpy)2(icpl)]Cl2 (Ru4) (phen=1,10-phenanthroline; bpy=2,2′-bipyridine; nmit=N-methyl-isatin-3-thiosemicarbazone, icpl=isatin-3-(4-Cl-phenyl)thiosemicarbazone) and [Ru(phen)2(aze)]Cl2 (Ru5), [Ru(bpy)2(aze)]Cl2 (Ru6) (aze=acetazolamide) and [Ru(phen)2(R-tsc)](ClO4)2 (R=methyl (Ru7), ethyl (Ru8), cyclohexyl (Ru9), 4-Cl-phenyl (10), 4-Br-phenyl (Ru11), and 4-EtO-phenyl (Ru12), tsc=thiosemicarbazone) were prepared and characterized by elemental analysis, FTIR, 1H-NMR and FAB-MS. Effect of these complexes on the growth of a transplantable murine tumor cell line (Ehrlich Ascites Carcinoma) and their antibacterial activity were studied. In cancer study the effect of hematological profile of the tumor hosts have also been studied. In the cancer study, the complexes Ru1—Ru4, Ru10 and Ru11 have remarkably decreased the tumor volume and viable ascitic cell count as indicated by trypan blue dye exclusion test (p<0.05). Treatment with the ruthenium complexes prolonged the lifespan of Ehrlich Ascites Carcinoma (EAC) bearing mice. Tumor inhibition by the ruthenium chelates was followed by improvements in hemoglobin, RBC and WBC values. All the complexes showed antibacterial activity, except Ru5 and Ru6. Thus, the results suggest that these ruthenium complexes have significant antitumor property and antibacterial activity. The results also reflect that the drug does not adversely affect the hematological profiles as compared to that of cisplatin on the host.

  为了寻找潜在的抗癌药物候选物，合成并表征了一系列单核钌配合物，包括[Ru(phen)2(nmit)]Cl2 (Ru1)、[Ru(bpy)2(nmit)]Cl2 (Ru2)、[Ru(phen)2(icpl)]Cl2 (Ru3)、[Ru(bpy)2(icpl)]Cl2 (Ru4)（其中phen=1,10-菲咯啉，bpy=2,2'-联吡啶，nmit=N-甲基-异氮茚-3-缩氨基硫脲，icpl=异氮茚-3-(4-氯苯基)缩氨基硫脲），以及[Ru(phen)2(aze)]Cl2 (Ru5)、[Ru(bpy)2(aze)]Cl2 (Ru6)（aze=醋唑磺胺）和[Ru(phen)2(R-tsc)](ClO4)2（R=甲基(Ru7)、乙基(Ru8)、环己基(Ru9)、4-氯苯基(Ru10)、4-溴苯基(Ru11)和4-乙氧基苯基(Ru12)，tsc=缩氨基硫脲）。研究了这些配合物对可移植的小鼠肿瘤细胞系（埃利希腹水癌）生长的影响及其抗菌活性。在癌症研究中，还研究了肿瘤宿主血液学特征的影响。在癌症研究中，配合物Ru1—Ru4、Ru10和Ru11显著减少了肿瘤体积和活腹水细胞数量，通过台阶蓝染色排斥试验显示（p<0.05）。使用这些钌配合物治疗延长了携带埃利希腹水癌（EAC）小鼠的寿命。钌配合物抑制肿瘤后，血红蛋白、红细胞和白细胞值有所改善。所有配合物都显示出抗菌活性，除了Ru5和Ru6。因此，结果表明这些钌配合物具有显著的抗肿瘤特性和抗菌活性。结果还反映出，与顺铂相比，该药物对宿主的血液学特征没有负面影响。
• Synthesis and Antimalarial Activity of Novel Dihydro-Artemisinin Derivatives
  作者：Yang Liu、Kunqiang Cui、Weiqiang Lu、Wei Luo、Jian Wang、Jin Huang、Chun Guo

  DOI：10.3390/molecules16064527

  日期：——

  The Plasmodium falciparum cysteine protease falcipain-2, one of the most promising targets for antimalarial drug design, plays a key role in parasite survival as a major peptide hydrolase within the hemoglobin degradation pathway. In this work, a series of novel dihydroartemisinin derivatives based on (thio)semicarbazone scaffold were designed and synthesized as potential falcipain-2 inhibitors. The

  恶性疟原虫半胱氨酸蛋白酶 falcipain-2 是抗疟药物设计中最有希望的靶点之一，作为血红蛋白降解途径中的主要肽水解酶，在寄生虫存活中起着关键作用。在这项工作中，设计并合成了一系列基于（硫代）缩氨基脲支架的新型双氢青蒿素衍生物作为潜在的 falcipain-2 抑制剂。体外生物测定表明，大多数目标化合物对 P. falciparum falcipain-2 显示出优异的抑制活性，IC(50) 值在 0.29-10.63 μM 范围内。进行分子对接研究以研究抑制剂的结合亲和力和相互作用模式。总结了初步的SARs，可以作为进一步研究抗疟药物开发的基础。
• 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。
• Lead Optimization of 2-Cyclohexyl-N-[(Z)-(3-methoxyphenyl/3-hydroxyphenyl) methylidene]hydrazinecarbothioamides for Targeting the HER-2 Overexpressed Breast Cancer Cell Line SKBr-3
  作者：Mashooq Bhat、Abdullah Al-Dhfyan、Ahmed Naglah、Azmat Khan、Mohamed Al-Omar

  DOI：10.3390/molecules201018246

  日期：——

  Lead derivatives of 2-cyclohexyl-N-[(Z)-(3-methoxyphenyl/3-hydroxyphenyl) methylidene]hydrazinecarbothioamides 1–18 were synthesized, characterized and evaluated in vitro against HER-2 overexpressed breast cancer cell line SKBr-3. All the compounds showed activity against HER-2 overexpressed SKBr-3 cells with IC50 = 17.44 ± 0.01 µM to 53.29 ± 0.33 µM. (2Z)-2-(3-Hydroxybenzylidene)-N-(3-methoxyphenyl)hydrazinecarbothioamide (12, IC50 = 17.44 ± 0.01 µM) was found to be most potent compound of this series targeting HER-2 overexpressed breast cancer cells compared to the standard drug 5-fluorouracil (5-FU) (IC50 = 38.58 ± 0.04 µM). Compound 12 inhibited the cellular proliferation via DNA degradation.

  合成并表征了 2-环己基-N-[(Z)-(3-甲氧基苯/3-羟基苯)亚甲基]肼硫酰胺的领先衍生物 1-18，并在体外评估其对 HER-2 过表达的乳腺癌细胞系 SKBr-3 的活性。所有化合物均对 HER-2 过表达的 SKBr-3 细胞显示出活性，IC50 范围为 17.44 ± 0.01 µM 到 53.29 ± 0.33 µM。发现 (2Z)-2-(3-羟基苄亚甲基)-N-(3-甲氧基苯)肼硫酰胺（12, IC50 = 17.44 ± 0.01 µM）是该系列中对 HER-2 过表达乳腺癌细胞最有效的化合物，相比于标准药物 5-氟尿嘧啶（5-FU）（IC50 = 38.58 ± 0.04 µM）。化合物 12 通过 DNA 降解抑制了细胞增殖。
• Synthesis of Thiosemicarbazone Derivatives of Benzo-15-crown-5 and Their Anion Recognition Properties
  作者：Yan-Qing Zhou、Tai-Bao Wei、You-Ming Zhang

  DOI：10.1080/10426500701681631

  日期：2008.5.14

  the solution change from colorless to yellow upon the addition of F−, these two points make it suitable to be used as colorimetric anion sensor to identify fluoride anion from other halide anions and carboxylate anions by naked-eye. The connection between receptor and anion is by hydrogen bonding interactions, the binding ratio is 1:1, which have been confirmed by UV-vis inspection spectra in CH3CN and

  以盐酸 (HCl) 为催化剂，在室温下高效合成了 benzo-15-crown-5 的一系列缩氨基硫脲衍生物。研究了它们对 a、b 和 c 的阴离子识别特性，结果表明它们对 CH3CN 中的 F−、MeCO2− 和 n-C3H7CO2− 表现出高度选择性的结合和感应 (F− > n-C3H7CO2 − > MeCO2 − > > Cl -、Br- 和 I-)。特别是受体c显示出不​​同的F−与MeCO2−和C3H7CO2−的UV-Vis光谱，除了加入F−后溶液颜色由无色变为黄色外，这两点使其适合用作比色法阴离子传感器，通过肉眼从其他卤化物阴离子和羧酸根阴离子中识别氟阴离子。受体与阴离子的连接是通过氢键相互作用，结合比例为1:1，