2-methylthio-2-imidazoline hydrochloride | 5734-12-3

• 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-methylthio-2-imidazoline hydrochloride
• 英文别名: 2-methylsulfanyl-4,5-dihydro-1H-imidazol-1-ium;chloride
• CAS: 5734-12-3
• 化学式: C₄H₈N₂S*ClH
• 分子量: 152.648
• InChiKey: NODDULJCYKABBP-UHFFFAOYSA-N

物化性质

• 熔点：
  171-172.6 °C

计算性质

• 辛醇/水分配系数(LogP)：
  0.73
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  2-(甲硫基)-2-咪唑啉 在 盐酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 12.0h， 以98%的产率得到2-methylthio-2-imidazoline hydrochloride
  参考文献：
  名称：

  温和条件下异硫脲碘化物和胺的鸟苷化合成五元和六元环胍

  摘要：

  摘要 通过异硫脲碘化物与等摩尔量的各种胺在四氢呋喃中反应，一步得到环状氢碘化胍。所得氢碘化物用氢氧化钠或阴离子交换树脂中和，以定量产率提供相应的取代环胍。图形概要

  DOI：

  10.1080/00397911.2016.1269927

文献信息

• [EN] INDAZOLE DERIVATIVES AS αV INTEGRIN ANTAGONISTS<br/>[FR] DÉRIVÉS D'INDAZOLE EN TANT QU'ANTAGONISTES DE L'INTÉGRINE αV
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2018089357A1

  公开（公告）日：2018-05-17

  The present invention provides compounds of Formula (Ia) or (Ib): or stereoisomers, tautomers, or pharmaceutically acceptable salts or solvates thereof, wherein all the variables are as defined herein. These compounds are antagonists to αV- containing integrins. This invention also relates to pharmaceutical compositions comprising these compounds and methods of treating a disease, disorder, or condition associated with dysregulation of αV-containing integrins, such as pathological fibrosis, transplant rejection, cancer, osteoporosis, and inflammatory disorders, by using the compounds and pharmaceutical compositions.

  本发明提供了式（Ia）或（Ib）的化合物：或其立体异构体、互变异构体或药学上可接受的盐或溶剂，其中所有变量如本文所定义。这些化合物是αV-含有整合素的拮抗剂。本发明还涉及包括这些化合物的药物组合物以及使用这些化合物和药物组合物治疗与αV-含有整合素失调相关的疾病、紊乱或状况的方法，如病理性纤维化、移植排斥、癌症、骨质疏松症和炎症性疾病。
• Synthesis and evaluation of 6-methylene-bridged uracil derivatives. Part 2: Optimization of inhibitors of human thymidine phosphorylase and their selectivity with uridine phosphorylase
  作者：Shingo Yano、Hideki Kazuno、Tsutomu Sato、Norihiko Suzuki、Tomohiro Emura、Konstanty Wierzba、Jun-ichi Yamashita、Yukio Tada、Yuji Yamada、Masakazu Fukushima、Tetsuji Asao

  DOI：10.1016/j.bmc.2004.04.046

  日期：2004.7

  A series of novel 6-methylene-bridged uracil derivatives have been optimized for clinical use as the inhibitors of human thymidine phosphorylase (TP). We describe their synthesis and evaluation. Introduction of a guanidino or an amidino group enhanced the in vitro inhibitory activity of TP comparing with formerly reported inhibitor 1. Their selectivity for TP based on uridine phosphorylase inhibitory

  已经优化了一系列新颖的6-亚甲基桥接的尿嘧啶衍生物，以作为人胸苷磷酸化酶（TP）的抑制剂用于临床。我们描述它们的综合和评估。与以前报道的抑制剂1相比，胍基或a基的引入增强了TP的体外抑制活性。还评估了它们基于尿苷磷酸化酶抑制活性对TP的选择性。化合物2（TPI）由于其强大的TP抑制作用和2'-脱氧-5-（三氟甲基）尿苷（F（3）dThd）药代动力学的出色调节作用，已被选择用于临床评估。结果，TAS-102（F（3）dThd和TPI的组合）目前处于1期临床研究中。
• Structure-Activity Relationship Modeling and Experimental Validation of the Imidazolium and Pyridinium Based Ionic Liquids as Potential Antibacterials of MDR Acinetobacter baumannii and Staphylococcus aureus
  作者：Ivan V. Semenyuta、Maria M. Trush、Vasyl V. Kovalishyn、Sergiy P. Rogalsky、Diana M. Hodyna、Pavel Karpov、Zhonghua Xia、Igor V. Tetko、Larisa O. Metelytsia

  DOI：10.3390/ijms22020563

  日期：——

  Online Chemical Modeling Environment (OCHEM) was used for QSAR analysis of a set of ionic liquids (ILs) tested against multi-drug resistant (MDR) clinical isolate Acinetobacter baumannii and Staphylococcus aureus strains. The predictive accuracy of regression models has coefficient of determination q2 = 0.66 − 0.79 with cross-validation and independent test sets. The models were used to screen a virtual chemical library of ILs, which was designed with targeted activity against MDR Acinetobacter baumannii and Staphylococcus aureus strains. Seven most promising ILs were selected, synthesized, and tested. Three ILs showed high activity against both these MDR clinical isolates.

  使用在线化学建模环境（OCHEM）对一组离子液体（ILs）进行了QSAR分析，这些ILs针对多药耐药（MDR）临床分离的阿氏不动杆菌和金黄色葡萄球菌菌株进行了测试。回归模型的预测准确度具有决定系数q2 = 0.66至0.79，通过交叉验证和独立测试集。这些模型被用来筛选一个虚拟的ILs化学库，该库设计用于针对MDR阿氏不动杆菌和金黄色葡萄球菌菌株的靶向活性。选择了七种最有前途的ILs，进行了合成和测试。其中三种ILs对这两种MDR临床分离物表现出高活性。
• 2-[4(3)-Amino-3(4)-hydroxyphenylimino]-imidazolines, useful in the
  申请人：Synthelabo

  公开号：US04492709A1

  公开（公告）日：1985-01-08

  Imidazolidine derivatives of the formula: ##STR1## wherein R.sub.1 represents the hydroxy radical and R.sub.2 represents a grouping --NHSO.sub.2 CH.sub.3, --NHCOR' or --NHCONR'R", R' and R" independently of one another representing a hydrogen atom or an alkyl radical having from 1 to 4 carbon atoms, or alternatively R.sub.2 represents the hydroxy radical and R.sub.1 represents a grouping --NHSO.sub.2 CH.sub.3, --NHCOR' or ?NHCONR'R", R' and R" independently of one another representing a hydrogen atom or an alkyl radical having from 1 to 4 carbon atoms, and pharmacologically-acceptable acid addition salts thereof, are new therapeutically useful compounds. They are more particularly useful in the treatment of gastric hypersecretion or hyperacidity or glaucoma.

  Imidazolidine衍生物的化学式为：##STR1## 其中R.sub.1代表羟基基团，R.sub.2代表--NHSO.sub.2 CH.sub.3、--NHCOR'或--NHCONR'R"基团，其中R'和R"各自独立表示氢原子或具有1至4个碳原子的烷基基团，或者R.sub.2代表羟基基团，R.sub.1代表--NHSO.sub.2 CH.sub.3、--NHCOR'或?NHCONR'R"基团，其中R'和R"各自独立表示氢原子或具有1至4个碳原子的烷基基团，并且其药学上可接受的酸盐是新的治疗有用化合物。它们特别适用于治疗胃分泌过多或过酸或青光眼。
• New QSTR models to evaluation of imidazolium- and pyridinium-contained ionic liquids toxicity
  作者：Ivan Semenyuta、Vasyl Kovalishyn、Diana Hodyna、Yuliia Startseva、Sergiy Rogalsky、Larysa Metelytsia

  DOI：10.1016/j.comtox.2024.100309

  日期：2024.6

  the creation of predictive models for toxicity evaluation of imidazolium- and pyridinium-containing ionic liquids. New created predictive models were developed using the OCHEM. The predictive ability of the models was tested by cross-validation, giving a coefficient of determination q = 0.77–0.82. The models were applied to screen a virtual chemical library to the toxicity of ILs in Danio rerio and

  我们提出了机器学习研究，致力于创建用于含咪唑鎓和吡啶鎓离子液体毒性评估的预测模型。新创建的预测模型是使用 OCHEM 开发的。通过交叉验证测试模型的预测能力，得出决定系数 q = 0.77–0.82。该模型用于筛选虚拟化学库，以了解斑马鱼和大型水蚤生物测定中离子液体的毒性。使用模型预测 25 种 IL 的毒性，然后合成并进行体内测试。体内毒性研究发现，D. magna 是一种比 D. rerio 更敏感的水生测试生物 – 67% 的研究 IL 被归类为剧毒，LC 范围为 0.005 至 0.01 mg/l。同时，使用斑马鱼作为测试生物，只有一种 LC 为 0.08 mg/l 的 IL 1-十二烷基溴化吡啶被归类为剧毒化合物，76% 被归类为轻度和中度毒性化合物。将毒性最强的 IL 5 和 19 对接至人 AChE 活性中心，计算得出的结合能值 -9.5 和 -9.3 kcal/mol，与人