1-(4-Chlorophenyl)-3-[1-(diethylamino)ethylidene]thiourea | 931098-08-7

• 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: 1-(4-Chlorophenyl)-3-[1-(diethylamino)ethylidene]thiourea
• 英文别名: 1-(4-chlorophenyl)-3-[1-(diethylamino)ethylidene]thiourea
• CAS: 931098-08-7
• 化学式: C₁₃H₁₈ClN₃S
• 分子量: 283.825
• InChiKey: YMYXYHDHZAAMIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(4-Chlorophenyl)-3-[1-(diethylamino)ethylidene]thiourea 在 盐酸羟胺 、 silver nitrate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以520 mg的产率得到N-(4-chlorophenyl)-5-methyl-1,2,4-oxadiazol-3-amine
  参考文献：
  名称：

  A Diversified Assembly of 1,2,4-Oxadiazol-3-amines: Metallic Thiophile Catalyzed Chemoselective One-Pot Reaction of Aryl Isothiocyanates, Amidines/Guanidines, and Hydroxylamine

  摘要：

  An efficient one-pot synthesis of 1,2,4-oxadiazol-3-amines from simple starting materials, isothiocyanates, amidines/guanidines, and hydroxylamine, is described. The reaction is facilitated by metallic-thiophile-assisted desulfurization of in situ formed amidino- or guanidinothiourea to give chemoselectively N-hydroxyguanidine intermediates that give exclusively various 1,2,4-oxadiazol-3-amines in good to excellent yields. The reaction mechanistic pathway may proceed through an intramolecular 5-exotrig cyclization.

  DOI：

  10.1055/s-0032-1317504
• 作为产物：
  描述：

  对氯苯胺 在 三乙胺 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 9.5h， 生成 1-(4-Chlorophenyl)-3-[1-(diethylamino)ethylidene]thiourea
  参考文献：
  名称：

  噻唑类分子作为抗癌药的设计，计算研究，合成和生物学评估

  摘要：

  背景 消除癌症保证了针对特定途径的有效治疗方式，这些途径在肿瘤增殖和存活中失调。抗凋亡的Bcl-2蛋白在几种肿瘤类型中发生了显着变化，将其定位为治疗干预的靶标。在这里，我们设计，计算评估，合成和生物学测试了结构优化的基于噻唑的小分子作为抗癌剂。 方法 虚拟设计的200个分子经过了严格的对接和计算机模拟ADME毒性研究。其中，使用便宜且容易获得的试剂分三步合成了23个通过泛分析干扰化合物（PAINS）过滤器并在合成上可行的基于骨架的噻唑类分子。分子是在体外针对Bcl-2的-的Jurkat，A-431癌细胞系和ARPE-19细胞系进行评估。进行了分子动力学（MD）模拟研究，以分析Bcl-2中配体32诱导的构象变化。对化合物32处理的Bcl-2细胞进行流式细胞术分析以检查细胞凋亡。 结果 该分子表现出与Bcl-2的明显相互作用，并具有可接受的药物样性质，如在计算机中测试的。多步合成以高达80％的

  DOI：

  10.1016/j.ejps.2019.04.005

文献信息

• A convenient one-pot synthesis of trisubstituted 1,3,5-triazines through intermediary amidinothioureas
  作者：Jitendra C. Kaila、Arshi B. Baraiya、Amit N. Pandya、Hitesh B. Jalani、V. Sudarsanam、Kamala K. Vasu

  DOI：10.1016/j.tetlet.2010.01.034

  日期：2010.3

  A thiophile-promoted one-pot synthesis of trisubstituted 1,3,5-triazines starting from isothiocyanates, N,N-diethylamidines, and carbamidines has been studied. The reaction proceeds through the formation of intermediary amidinothioureas, which react with carbamidines in the presence of mercury(II) chloride to generate the desired 1,3,5-triazines in good to moderate yields (40–70%).

  已研究了由异硫氰酸酯，N，N-二乙基am和尿素起始的由噻吩促进的一锅合成三取代1,3,5-三嗪。该反应通过形成中间体a基硫脲而进行，该中间体在氯化汞（II）的存在下与氨基甲酰胺反应生成所需的1,3,5-三嗪，并具有良好至中等的收率（40-70％）。
• Mercury(II) Chloride-Mediated Desulphurization of Amidinothioureas: Synthesis and Antimicrobial Activity of 3-Amino-1,2,4-triazole Derivatives
  作者：Swapnil G. Yerande、Chetna D. Baviskar、Kiran M. Newase、Wei Wang、Kan Wang、Alexander Dömling

  DOI：10.1002/jhet.1890

  日期：2014.11

  The synthesis of 3‐amino‐1,2,4‐triazole via mercury(II) chloride‐mediated cyclization of amidinothiourea is described. This procedure offers a general and efficient route to synthesize the title compound by 3 + 2 annulation reaction. On the basis of the literature precedence, the mechanism for the formation of 3‐amino‐1,2,4‐triazole is proposed. When the synthesized compounds were tested for their

  描述了通过氯化汞（II）介导的thio硫脲的环化反应，合成3-氨基1,2,4-三唑。该程序提供了通过3 + 2环化反应合成标题化合物的一般有效途径。根据文献的优先次序，提出了3-氨基1,2,4-三唑的形成机理。当测试合成的化合物的抗微生物活性时，对被测试的微生物显示出有希望的抑制作用。
• Discovery of 2-aminoimidazole and 2-amino imidazolyl-thiazoles as non-xanthine human adenosine A₃receptor antagonists: SAR and molecular modeling studies
  作者：Amit N. Pandya、Arshi B. Baraiya、Hitesh B. Jalani、Dhaivat Pandya、Jitendra C. Kaila、Sonja Kachler、Veronica Salmaso、Stefano Moro、Karl-Norbert Klotz、Kamala K. Vasu

  DOI：10.1039/c7md00643h

  日期：——

  le derivatives was synthesized using a 2-chloro trityl resin. The generated compound library was tested against all the human adenosine receptors subtypes. The 2-aminoimidazole derivatives (6a–6l) showed weak to moderate affinity towards the human adenosine receptors. Further modification to 2-aminoimidazolyl-thiazole derivatives (12a–12l) resulted in an improvement of affinity at adenosine A1, A2A

  使用2-氯三苯甲基树脂合成了24种具有2-氨基咪唑和2-氨基咪唑基-噻唑衍生物的化合物的小分子组合库。针对所有人类腺苷受体亚型对生成的化合物库进行了测试。2-氨基咪唑衍生物（6a-6l）对人腺苷受体的亲和力较弱。对2-氨基咪唑基-噻唑衍生物（12a-12l）的进一步修饰导致对腺苷A 1，A 2A和A 3受体亚型的亲和力提高。化合物12b是最有效和选择性最高的非黄嘌呤人腺苷A 3该系列的受体拮抗剂。进行了基于受体的建模研究，以探索这些新型2-氨基咪唑和2-氨基咪唑基-噻唑衍生物与人腺苷A 1，A 2A和A 3受体亚型的可能结合方式。
• Design, synthesis and characterization of novel 2-(2,4-disubstituted-thiazole-5-yl)-3-aryl-3H-quinazoline-4-one derivatives as inhibitors of NF-κB and AP-1 mediated transcription activation and as potential anti-inflammatory agents
  作者：Rajan S. Giri、Hardik M. Thaker、Tony Giordano、Jill Williams、Donna Rogers、Vasudevan Sudersanam、Kamala K. Vasu

  DOI：10.1016/j.ejmech.2008.10.031

  日期：2009.5

  A series of 2-(2,4-disubstituted-thiazole-5-yl)-3-aryl-3H-quinazoline-4-one derivatives were designed and synthesized. Synthesized molecules were further evaluated for their inhibitory activity towards transcription factors NF-kappa B and AP-1 mediated transcriptional activation in a cell line based in vitro as well as for their anti-inflammatory activity in in vivo model of acute inflammation. This series provides us with selective and dual inhibitors of NF-kappa B and AP-1 mediated transcriptional activation which also exhibit significant efficacy in in vivo model of inflammation. Two of the compounds 9m and 9o turned out to be the most promising dual inhibitors of NF-kappa B and AP-1 mediated transcriptional activation with an IC50 of 3.3 mu M for both. 9n (IC50 = 5.5 mu M) and 9p (IC50 = 5.5 mu M) emerged as selective inhibitors of NF-kappa B mediated transcriptional activation and 9c (IC50 = 5.5 mu M) and 9d (IC50 = 5.5 mu M) were found to be more selective inhibitor of AP-1 mediated transcriptional activity. Though the relationship between the activities shown by these compounds in in vivo and in vitro model is still to be established, these results suggest the suitability of the designed molecular framework as a potential anti-inflammatory molecular framework which also exhibits the inhibitory activity towards NF-kappa B and AP-1 mediated transcriptional activation. This will be worth studying further to explore its complete potential particularly in chronic inflammatory conditions. The structure activity relationship (SAR) of this series has been discussed herein. (C) 2008 Elsevier Masson SAS. All rights reserved.
• A facile synthesis of structurally novel 1-aryl-2-arylamino-4-alkyl/phenyl-5-aroyl-1H-imidazoles from amidinothioureas
  作者：Jitendra C. Kaila、Arshi B. Baraiya、Kamala K. Vasu、V. Sudarsanam

  DOI：10.1016/j.tetlet.2008.10.012

  日期：2008.12

  We report here a convenient and efficient two-step synthesis of 1-aryl-2-arylamino-4-alkyl/phenyl-5-aroyl-1H-imidazoles from easily available amidinothioureas. Guanylation of amidinothioureas 1 using mercury(II) chloride as a thiophile yielded amidinoguanidines 2, which reacted with various phenacyl bromides under mild conditions to afford the corresponding diversely functionalized imidazoles 3 in moderate to good yields. (C) 2008 Elsevier Ltd. All rights reserved.