2-hydrazinyl-4,5-dihydro-1H-imidazole dihydrochloride | 49541-78-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: 2-hydrazinyl-4,5-dihydro-1H-imidazole dihydrochloride
• 英文别名: 2-hydrazino-2-imidazoline dihydrochloride；2-hydrazino-1,3-diazacyclopent-2-ene dihydrochloride；2-Hydrazino-2-imidazoline, dihydrochloride；2-hydrazinoimidazoline dihydrochloride；2-Hydrazinyl-4,5-dihydro-1H-imidazole hydrochloride；4,5-dihydro-1H-imidazol-2-ylhydrazine;hydrochloride
• CAS: 49541-78-8；61566-22-1
• 化学式: C₃H₈N₄*2ClH
• 分子量: 173.045
• InChiKey: ORDLJERQKZRBRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.17
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  62.4
• 氢给体数：
  4
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Benzo<1,2-b:4,5-b'>dithiophene-4,8-dicarboxaldehyde 、 2-hydrazinyl-4,5-dihydro-1H-imidazole dihydrochloride 以 丙醇 为溶剂， 反应 1.0h， 以12%的产率得到Benzo<1,2-b:4,5-b'>dithiophene-4,8-dicarboxaldehyde Bis(2-imidazolin-2-ylhydrazone) Dihydrochloride
  参考文献：
  名称：

  比森丁烯杂环类似物的合成

  摘要：

  蒽-9,10-二甲醛的双鸟嘌呤hydr已显示出优异的抗肿瘤活性。合成杂环类似物以扩大或改变活性谱。

  DOI：

  10.1002/jhet.5570250656
• 作为产物：
  描述：

  2-methylthio-2-imidazoline hydrochloride 在 一水合肼 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 以88.4%的产率得到2-hydrazinyl-4,5-dihydro-1H-imidazole dihydrochloride
  参考文献：
  名称：

  Synthesis and DNA cleavage activity of 2-hydrazinyl-1,4,5,6-tetrahydropyrimidine containing hydroxy group

  摘要：

  2-Hydrazinyl-1,4,5,6-tetrahydropyrimidin-5-ol dihydrochloride 2, as well as 2-hydrazinyl-4,5-dihydro-1H-imidazole dihydrochloride 1, was synthesized as metal-free DNA cleaving agent. Agarose gel electrophoresis was used to assess the plasmid pUC 19 DNA cleavage activities in the presence of 1 and 2. DNA cleavage efficiency of 2 exhibits remarkable increases compared with its corresponding non-hydroxy compound 1. Kinetic data of DNA cleavage promoted by 2 fit to the Michaelis-Menten-type equation with k(max) of 0.0378 +/- 0.0013 h (1)giving 10(6)-fold rate acceleration over uncatalyzed DNA. The acceleration is driven by the spatial proximity of the nucleophilic hydroxy group and the electrophilic activation for the phosphodiester by the ammonium and/or guanidinium groups. In vitro cytotoxic activities toward Hela cells and human leukemia HL-60 cells were also examined, and 2 exhibits stronger cytotoxic activities than 1. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2009.05.044

文献信息

• THERAPEUTIC COMPOUNDS
  申请人：REGENTS OF THE UNIVERSITY OF MINNESOTA

  公开号：US20180230105A1

  公开（公告）日：2018-08-16

  The invention provides compounds of formula Ia′, Ib′, Ic′, and Id′: and pharmaceutically acceptable salts thereof, wherein the variables A, R 6 , R 7 , R 8 , R 9 , R x , L, X, Y, and Z have the meaning as described herein. The compounds are useful for reducing endoplasmic reticulum stress and for producing analgesia in an animal.

  该发明提供了式Ia′、Ib′、Ic′和Id′的化合物及其药学上可接受的盐，其中变量A、R6、R7、R8、R9、Rx、L、X、Y和Z的含义如本文所述。这些化合物对于减少内质网应激并在动物体内产生镇痛作用是有用的。
• Process for preparing 2-hydrazino-1,3-diazacycloalk-2-ene hydrohalides
  申请人：American Cyanamid Company

  公开号：US04574155A1

  公开（公告）日：1986-03-04

  This invention provides a process for preparing a 2-hydrazino-1,3-diazacycloalk-2-ene hydrohalide. The process comprises reacting a one molar proportion of either tautomeric isomer of a 2-nitroamino-1,3-diazacycloalk-2-ene represented by the following formulas: ##STR1## wherein R.sup.1 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 hydroxyalkyl, C.sub.1 -C.sub.6 alkoxyalkyl, phenyl, substituted phenyl, benzyl, or substituted benzyl, R.sup.2 and R.sup.3 are independently hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkoxyalkyl, hydroxyl, aryl, substituted aryl, aralkyl and substituted aralkyl, and n is an integer from 0 to 3 with about an equimolar proportion of an ammonium halide or hydrazonium halide, and about a 1 to 2 molar proportion of hydrazine hydrate in a composition selected from a C.sub.1 to C.sub.4 aliphatic alcohol, water or a mixture thereof, at a temperature from about ambient to the reflux, and isolating the end product as a monohydrohalide. This invention also provides a process for preparing a 2-hydrazino-1,3-diazacycloalk-2-ene dihydrohalide. The process comprises reacting a compound of the formula: ##STR2## wherein R.sup.1 is hydrogen, C.sub.1 to C.sub.6 alkyl, or C.sub.1 to C.sub.6 hydroxyalkyl, R.sup.2 and R.sup.3 are independently hydrogen or C.sub.1 to C.sub.6 alkyl, n is 0 to 3 and X is a halide ion, with hydrogen halide wherein the halide ion is the same as defined above in a C.sub.1 to C.sub.4 alkyl alcohol at about 0.degree. to 30.degree. C.; and recovering the corresponding 2-hydrazino-1,3-diazacycloalk-2-ene dihydrohalide.

  这项发明提供了一种制备2-叠氮基-1,3-二氮杂环戊-2-烯氢卤化物的过程。该过程包括将由以下结构式表示的2-硝基氨基-1,3-二氮杂环戊-2-烯的两种互变异构体之一的1摩尔比例与约相等摩尔比例的铵盐卤化物或叠氮盐卤化物以及约1到2摩尔比例的叠氮水合物在选择自C1至C4脂肪醇、水或二者混合物的组合物中，以约室温至沸点的温度反应，并将终产物作为单氢卤化物进行分离。该发明还提供了一种制备2-叠氮基-1,3-二氮杂环戊-2-烯二氢卤化物的过程。该过程包括将具有以下结构式的化合物：其中R1为氢、C1到C6烷基或C1到C6羟基烷基，R2和R3独立地为氢或C1到C6烷基，n为0到3，X为卤化物离子，与卤化氢在约0°C至30°C的C1到C4烷基醇中反应；并回收相应的2-叠氮基-1,3-二氮杂环戊-2-烯二氢卤化物。
• A Convenient Approach to CF₃-Containing N-Heterocycles Based on 2-Methoxy-2-methyl-5-(trifluoromethyl)furan-3(2<i>H</i>)-one
  作者：Denis N. Bazhin、Yulia S. Kudyakova、Gerd-Volker Röschenthaler、Yanina V. Burgart、Pavel A. Slepukhin、Maksim L. Isenov、Victor I. Saloutin、Valery N. Charushin

  DOI：10.1002/ejoc.201500737

  日期：2015.8

  New synthetic routes to trifluoromethylated N-heterocycles based on condensations of 2-methoxy-2-methyl-5-(trifluoromethyl)furan-3(2H)-one with bifunctional N-nucleophiles are described. For the first time, trifluoromethyl-containing pyrazoles, pyrazolines and isoxazolines bearing hydrazone or oxime groups could be obtained by a one-pot strategy based on reactions of 5-(trifluoromethyl)furan-3(2H)-one

  描述了基于 2-甲氧基-2-甲基-5-(三氟甲基)呋喃-3(2H)-one 与双功能 N-亲核试剂缩合的三氟甲基化 N-杂环的新合成路线。首次通过基于 5-(三氟甲基)呋喃-3(2H)-one 与两当量相应的反应的一锅策略获得含三氟甲基的吡唑、吡唑啉和带有腙或肟基的异恶唑啉。肼或羟胺在酸存在下。呋喃-3(2H)-one 与尿素的相互作用在温和条件下进行，以良好的收率提供 1H-呋喃 [2,3-d]咪唑-2(3H)-one 衍生物。此外，通过呋喃-3(2H)-酮与邻苯二胺缩合得到含三氟甲基的喹喔啉衍生物。
• New Antitumor Imidazo[2,1-<i>b</i>]thiazole Guanylhydrazones and Analogues¹
  作者：Aldo Andreani、Silvia Burnelli、Massimiliano Granaiola、Alberto Leoni、Alessandra Locatelli、Rita Morigi、Mirella Rambaldi、Lucilla Varoli、Natalia Calonghi、Concettina Cappadone、Giovanna Farruggia、Maddalena Zini、Claudio Stefanelli、Lanfranco Masotti、Norman S. Radin、Robert H. Shoemaker

  DOI：10.1021/jm701246g

  日期：2008.2.1

  The synthesis of new antitumor 6-substituted imidazothiazole guanylhydrazones is described. Moreover, a series of compounds with a different basic chain at the 5 position were prepared. Finally, the replacement of the thiazole ring in the imidazothiazole system was also considered. All the new compounds prepared were submitted to the NCI cell line screen for evaluation of their antitumor activity. A few selected compounds were submitted to additional biological studies concerning effects on the cell cycle, apoptosis, and mitochondria.
• The synthesis of heterocyclic analogs of bisantrene
  作者：T. L. Fields、Yang-i Lin、J. D. Warren、S. A. Lang

  DOI：10.1002/jhet.5570250656

  日期：1988.11

  Bisguanylhydrazones of anthracene-9,10-dicarboxaldehyde have demonstrated excellent antitumor activity. Heterocyclic analogs were synthesized in an effort to expand or modify the activity profile.

  蒽-9,10-二甲醛的双鸟嘌呤hydr已显示出优异的抗肿瘤活性。合成杂环类似物以扩大或改变活性谱。