N-(1-o-tolyl-ethylidene)hydrazinecarboxylic acid ethyl ester | 449758-08-1

• 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: N-(1-o-tolyl-ethylidene)hydrazinecarboxylic acid ethyl ester
• 英文别名: N'-(1-o-tolyl-ethylidene)-hydrazinecarboxylic acid ethyl ester；ethyl N-[1-(2-methylphenyl)ethylideneamino]carbamate
• CAS: 449758-08-1
• 化学式: C₁₂H₁₆N₂O₂
• 分子量: 220.271
• InChiKey: ZIHDNHYLMZDDJP-UHFFFAOYSA-N

物化性质

• 熔点：
  115 °C
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  50.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(1-o-tolyl-ethylidene)hydrazinecarboxylic acid ethyl ester 在 N-溴代丁二酰亚胺(NBS) 、 氯化亚砜 、 sodium azide 、 偶氮二异丁腈 、 水 、 三苯基膦 作用下， 以 四氢呋喃 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 2-[1,2,3]thiadiazol-4-yl-benzylamine
  参考文献：
  名称：

  Discovery and Evaluation of Potent P₁ Aryl Heterocycle-Based Thrombin Inhibitors

  摘要：

  In an effort to discover potent, clinically useful thrombin inhibitors, a rapid analogue synthetic approach was used to explore the P-1 region. Various benzylamines were coupled to a pyridine/pyrazinone P-2-P-3 template. One compound with an o-thiadiazole benzylic substitution was found to have a thrombin K-i of 0.84 nM. A study of ortho-substituted five-membered-ring heterocycles was undertaken and subsequently demonstrated that the o-triazole and tetrazole rings were optimal. Combination of these potent P-1 aryl heterocycles with a variety of P-2-P-3 groups produced a compound with an extraordinary thrombin inhibitory activity of 1.4 pM. It is hoped that this potency enhancement in P-1 will allow for more diversification in the P-2-P-3 region to ultimately address additional pharmacological concerns.

  DOI：

  10.1021/jm030303e
• 作为产物：
  描述：

  1-甲基苯基乙酮 在 对甲苯磺酸一水合物 作用下， 以 甲苯 为溶剂， 生成 N-(1-o-tolyl-ethylidene)hydrazinecarboxylic acid ethyl ester
  参考文献：
  名称：

  Thrombin inhibitors

  摘要：

  该发明的化合物在抑制凝血酶、治疗血液凝固和心血管疾病方面具有用处，并具有以下结构： 1 其中 R 3 为氢或卤素，u为N或CH。

  公开号：

  US20020193398A1

文献信息

• Identification of a series of 1,3,4-trisubstituted pyrazoles as novel hepatitis C virus entry inhibitors
  作者：Jong Yeon Hwang、Hee-Young Kim、Dong-Sik Park、Jihyun Choi、Sung Min Baek、Keumhyun Kim、Soohyun Kim、Sikwang Seong、Inhee Choi、Hong-gun Lee、Marc Peter Windisch、Jinhwa Lee

  DOI：10.1016/j.bmcl.2013.09.039

  日期：2013.12

  In this report we describe the identification of novel pyrazole analogs as potent hepatitis C virus (HCV) entry inhibitor. The pyrazoles were identified by our phenotypic high-throughput screening using infectious HCV. A series of pyrazole derivatives was synthesized and evaluated for inhibitory activity against HCV in the infectious cell culture system. Through evaluation of selected compounds we

  在本报告中，我们描述了新型吡唑类似物作为强效丙型肝炎病毒（HCV）进入抑制剂的鉴定。通过使用感染性HCV的表型高通量筛选来鉴定吡唑。合成了一系列吡唑衍生物，并评估了其在感染性细胞培养系统中对HCV的抑制活性。通过评估选定的化合物，我们观察到吡唑不会干扰HCV RNA复制，但会干扰病毒进入，如分别使用HCV复制子和HCV假颗粒进行的实验所示。
• 1,2,3-Thiadiazole as a Modifiable and Scalable Directing Group for <i>ortho</i>-C–H Functionalization
  作者：Xiaoyan Jia、Donghui Xing、Jiayi Shen、Bo Li、Yue Zeng、Huanfeng Jiang、Liangbin Huang

  DOI：10.1021/acs.orglett.3c04075

  日期：2024.3.1

  modifiable directing group for C–H amidation and alkynylation with dioxazolones, p-toluenesulfonyl azide, and bromoalkynes in high yield. The densely functionalized 1,2,3-thiadiazole products are modified into thioamide, multisubstituted furan, γ-thiapyrone, thiazole, and various alkynyl sulfides through simple and one-step reactions. The competition experiments reveal that the directing ability of 1,2,3-thiadiazole

  在过去的几十年里，定向C-H键功能化在学术界和工业界具有巨大的应用前景。在 C-H 官能化中，非常需要开发一种新颖的、易于获得的、可扩展的、具有可修改能力的导向基团。在此，我们报道了 1,2,3-噻二唑作为可修饰的导向基团，用于与二恶唑酮、对甲苯磺酰叠氮和溴代炔进行 C-H 酰胺化和炔基化，产率高。通过简单的一步反应，将密集功能化的1,2,3-噻二唑产品改性为硫代酰胺、多取代呋喃、γ-噻吡酮、噻唑和各种炔基硫醚。竞争实验表明，1,2,3-噻二唑的定向能力略弱于吡啶和二齿酰胺，但强于广泛使用的羧酸盐。
• Discovery and Evaluation of Potent P₁ Aryl Heterocycle-Based Thrombin Inhibitors
  作者：Mary Beth Young、James C. Barrow、Kristen L. Glass、George F. Lundell、Christina L. Newton、Janetta M. Pellicore、Kenneth E. Rittle、Harold G. Selnick、Kenneth J. Stauffer、Joseph P. Vacca、Peter D. Williams、Dennis Bohn、Franklin C. Clayton、Jacquelynn J. Cook、Julie A. Krueger、Lawrence C. Kuo、S. Dale Lewis、Bobby J. Lucas、Daniel R. McMasters、Cynthia Miller-Stein、Beth L. Pietrak、Audrey A. Wallace、Rebecca B. White、Bradley Wong、Youwei Yan、Philippe G. Nantermet

  DOI：10.1021/jm030303e

  日期：2004.6.1

  In an effort to discover potent, clinically useful thrombin inhibitors, a rapid analogue synthetic approach was used to explore the P-1 region. Various benzylamines were coupled to a pyridine/pyrazinone P-2-P-3 template. One compound with an o-thiadiazole benzylic substitution was found to have a thrombin K-i of 0.84 nM. A study of ortho-substituted five-membered-ring heterocycles was undertaken and subsequently demonstrated that the o-triazole and tetrazole rings were optimal. Combination of these potent P-1 aryl heterocycles with a variety of P-2-P-3 groups produced a compound with an extraordinary thrombin inhibitory activity of 1.4 pM. It is hoped that this potency enhancement in P-1 will allow for more diversification in the P-2-P-3 region to ultimately address additional pharmacological concerns.
• Thrombin inhibitors
  申请人：——

  公开号：US20020193398A1

  公开（公告）日：2002-12-19

  Compounds of the invention are useful in inhibiting thrombin and treating blood coagulation and cardiovascular disorders and have the following structure: 1 wherein R 3 is hydrogen or halogen, and u is N or CH.

  该发明的化合物在抑制凝血酶、治疗血液凝固和心血管疾病方面具有用处，并具有以下结构： 1 其中 R 3 为氢或卤素，u为N或CH。