1-carbamimidoyl-2-methyl-isothiourea hydroiodide | 14945-92-7

• 物质功能分类: 医药中间体 - 原料药中间体
• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-carbamimidoyl-2-methyl-isothiourea hydroiodide
• 英文别名: 1-[Amino(methylsulfanyl)methylidene]guanidine hydroiodide；methyl N-(diaminomethylidene)carbamimidothioate;hydroiodide
• CAS: 14945-92-7
• 化学式: C₃H₈N₄S*HI
• mdl: MFCD23144068
• 分子量: 260.102
• InChiKey: PGWVITGVIBSMTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.25
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  115
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-carbamimidoyl-2-methyl-isothiourea hydroiodide 、 4-氨基丁酸 在 三乙胺 作用下， 以 乙醇 、 水 为溶剂， 反应 12.0h， 以25%的产率得到4-{[{[Amino(imino)methyl]amino}(imino)methyl]amino}butanoic acid
  参考文献：
  名称：

  Synthesis and Biological Activity of Aminoguanidine and Diaminoguanidine Analogues of the Antidiabetic/Antiobesity Agent 3-Guanidinopropionic Acid

  摘要：

  3-Guanidinopropionic acid (1) has been demonstrated both to improve insulin sensitivity and to promote weight loss selectively from adipose tissue in animal models of non-insulin-dependent diabetes mellitus (NIDDM). However, 1 has also been shown to be a substrate for both the creatine transporter and creatine kinase, leading to marked accumulation in muscle tissue as the corresponding N-phosphate. The corresponding aminoguanidine analogue 2 was recently discovered to retain the antidiabetic activity of 1 while being markedly less susceptible to creatine-like metabolism, suggesting that it should have less potential to accumulate in muscle. Further structural modification of 2 was undertaken to investigate whether the antidiabetic potency could be augmented while maintaining resistance to creatine-like metabolism. Modifications such as a-alkylation, homologation, and bioisosteric replacement of the aminoguanidine all were detrimental to antidiabetic activity. However, the simple regioisomeric aminoguanidinoacetic acid 9 and diaminoguanidinoacetic acid-analogue 7 were found to be equipotent to 2, leading eventually to the discovery of the significantly more potent diaminoguanidinoacetic acid regioisomers 52 and 53. Further attempts to modify the more active template represented by 52 led only to reductions in; antidiabetic activity. Each of the new active analogues displayed the same resistance to creatine-like metabolism as 2. Further testing of 7, 9, and 53 in obese diabetic ob;lob mice confirmed that weight loss is induced selectively from adipose tissue, similar to the lead 1. Administration of 53 to insulin-resistant rhesus monkeys led to reductions in both fasting and post-prandial plasma glucose levels with concomitant reductions in plasma insulin levels, suggesting that the compound improved the action of endogenous insulin. Compounds 7 and 53 were selected for further preclinical development.

  DOI：

  10.1021/jm000094n
• 作为产物：
  描述：

  脒基硫脲 、 碘甲烷 以 乙醇 为溶剂， 反应 2.0h， 生成 1-carbamimidoyl-2-methyl-isothiourea hydroiodide
  参考文献：
  名称：

  Novel Compounds Containing Multiple Guanide Groups That Bind the HIV Coreceptor CXCR4

  摘要：

  摘要 G 蛋白偶联受体 CXCR4 是人类免疫缺陷病毒 1 型（HIV-1）感染的核心受体，并参与细胞迁移和增殖的信号传递。阻断 CXCR4 相互作用的化合物有可能用作 HIV 进入抑制剂，以补充马拉维若等阻断替代核心受体 CCR5 的药物，或用于癌症治疗。多肽 T140 含有五个精氨酸残基，是迄今为止开发的最有效的 CXCR4 拮抗剂。在寻找可抑制 HIV 进入的非肽 CXCR4 配体的过程中，我们从 12 个含有 2、3、4、6 或 8 个氨基的线性和支链多胺中合成了三个系列的化合物，并将其取代以产生相应的胍类、双胍类或苯基胍类。测试了所得化合物与 T140 竞争结合哺乳动物细胞上表达的人类 CXCR4 受体的能力。最有效的化合物与 CXCR4 结合的 50% 抑制浓度为 200 nM，而且所有化合物的细胞毒性都很低。然后测试了两个系列的化合物抑制 TZM-bl 细胞感染 X4 和 R5 株 HIV-1 的能力。在低微摩尔浓度下，精胺苯胍和亚精胺苯胍能抑制 X4 株的感染，但不能抑制 R5 株的感染。这些结果支持进一步研究和开发这些化合物作为 HIV 进入抑制剂。

  DOI：

  10.1128/aac.00709-10

文献信息

• [EN] FUSED BICYCLIC ALKYLENE LINKED IMIDODICARBONIMIDIC DIAMIDES, METHODS FOR SYNTHESIS, AND USES IN THERARY<br/>[FR] DIAMIDES IMIDODICARBONIMIDIQUES LIÉS À UN ALKYLÈNE BICYCLIQUE FUSIONNÉ, PROCÉDÉS DE SYNTHÈSE ET UTILISATIONS DANS UNE THÉRAPIE
  申请人：NOVATARG INC

  公开号：WO2018106907A1

  公开（公告）日：2018-06-14

  The present invention provides novel fused bicyclic alkylene linked imidodicarbonimidic diamides. In particular, described herein are N-[2-(indol-3- yl)alkylene]-linked imidodicarbonimidic diamides and N-[2-(pyrrolopyridin-3- yl)alkylene]-linked imidodicarbonimidic diamides (compound of formula (I) or formula (II)), and uses therefor. The compounds of the present invention are believed to be organic cation transporter selective compounds, useful for the treatment of diseases and conditions caused by reduced activity of 5' adenosine monophosphate-activated protein kinase (AMPK).

  本发明提供了新型的融合的双环烷基亚乙基连接的咪唑二氨基碳亚胺二酰胺。具体来说，本文描述了N-[2-(吲哚-3-基)烷基]-连接的咪唑二氨基碳亚胺二酰胺和N-[2-(吡咯吡啶-3-基)烷基]-连接的咪唑二氨基碳亚胺二酰胺（化合物的结构式（I）或结构式（II）），以及其用途。本发明的化合物被认为是有机阳离子转运体选择性化合物，可用于治疗由于5'腺苷单磷酸活化蛋白激酶（AMPK）活性降低而引起的疾病和症状。
• [EN] HERBICIDAL COMBINATION COMPRISING AZINES<br/>[FR] COMBINAISON HERBICIDE COMPRENANT DES AZINES
  申请人：BASF SE

  公开号：WO2015162164A1

  公开（公告）日：2015-10-29

  The present invention relates to herbicidal combinations comprising at least one compound of formula (I) (component a) and at least one further compound selected from herbicidally active compounds (component b) and/or safeners (component c) wherein Ra, Rb, Rc, Rd are inter alia H, halogen, CN, NO2, C1-C6-alkyl, C1-C6-haloalkyl, OH, C1-C6-alkoxy, C1-C6-alkylthio, etc.; R1 is inter alia H, OH, S(O)2NH2, CN, C1-C6-alkyl, etc.; R2 is inter alia H, halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C3-C6- alkynyl, etc.; R3 is inter alia H, halogen, CN, C1-C6-alkyl, etc; R4 is inter alia H, halogen, CN, C1-C6-alkyl, etc; or R3 and R4 together with the carbon atom to which they are attached form a moiety selected from the group consisting of carbonyl, C2-C6-alkenyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl and three- to six-membered heterocyclyl, and R5 is inter alia H, OH, S(O)2NH2, CN, C1-C6-alkyl, etc; including their agriculturally acceptable salts or N-oxides; and at least one further compound selected from herbicide compounds b) and safeners c) and mixtures thereof.

  本发明涉及除草剂组合物，其中包括至少一种式(I)的化合物（成分a），以及至少一种从具有除草活性的化合物（成分b）和/或安全剂（成分c）中选择的进一步化合物，其中Ra、Rb、Rc、Rd等为H、卤素、CN、NO2、C1-C6-烷基、C1-C6-卤代烷基、OH、C1-C6-烷氧基、C1-C6-烷基硫基等；R1等为H、OH、S（O）2NH2、CN、C1-C6-烷基等；R2等为H、卤素、CN、C1-C6-烷基、C1-C6-卤代烷基、C2-C6-烯基、C3-C6-炔基等；R3等为H、卤素、CN、C1-C6-烷基等；R4等为H、卤素、CN、C1-C6-烷基等；或者R3和R4与它们连接的碳原子一起形成从羰基、C2-C6-烯基、C3-C6-环烷基、C3-C6-环烯基和三至六元杂环烷基中选择的基团；R5等为H、OH、S（O）2NH2、CN、C1-C6-烷基等；包括它们的农业上可接受的盐或N-氧化物；以及至少一种从除草剂化合物b）和安全剂c）中选择的进一步化合物以及它们的混合物。
• [EN] DIAMINOTRIAZINE COMPOUNDS<br/>[FR] COMPOSÉS DE DIAMINOTRIAZINE
  申请人：BASF SE

  公开号：WO2020058009A1

  公开（公告）日：2020-03-26

  The present invention relates to diaminotriazine compounds and to their use as herbicides. It also relates to agrochemical compositions for crop protection and to a method for controlling unwanted vegetation.

  本发明涉及二氨基三嗪化合物及其作为除草剂的用途。它还涉及用于作物保护的农药组合物以及控制不良植被的方法。
• [EN] HERBICIDAL AZINES<br/>[FR] AZINES HERBICIDES
  申请人：BASF SE

  公开号：WO2014064094A1

  公开（公告）日：2014-05-01

  The present invention relates t oazines of formula (I) wherein the variables are defined according to the description, processes and intermediated for preparing them, compositions comprising them and their use as herbicides, i.e. for controlling harmful plants and a method for controlling unwanted vegetation which comprises allowing a herbicidal effective amount of at least one azine of the formula I to act on plants, their seed and/or their habitat.

  本发明涉及式(I)的腙类化合物，其中变量根据说明书定义，用于制备它们的过程和中间体，包括它们的组合物以及它们作为除草剂的用途，即用于控制有害植物和一种控制不受欢迎的植被的方法，其中包括让式(I)中至少一种腙类化合物的除草有效量作用于植物、它们的种子和/或它们的生境。
• [EN] DIAMINOTRIAZINE DERIVATIVES AS HERBICIDES<br/>[FR] DÉRIVÉS DE DIAMINOTRIAZINE UTILISÉS COMME HERBICIDES
  申请人：BASF SE

  公开号：WO2015155273A1

  公开（公告）日：2015-10-15

  The present invention relates to diaminotriazine compounds of the formula (I) and to their use as herbicides. The present invention also relates to agrochemical compositions for crop protection and to a method for controlling unwanted vegetation.

  本发明涉及式(I)的二氨基三嗪化合物及其作为除草剂的用途。本发明还涉及用于作物保护的农药组合物以及控制不良植被的方法。