N-氰基-N'-(2-巯基乙基)-N''-甲基胍 | 61085-25-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: N-氰基-N'-(2-巯基乙基)-N''-甲基胍
• 英文名称: N-cyano-N'-methyl-N"-(2-mercaptoethyl)-guanidine
• 英文别名: N-cyano-N'-methyl-N"-(2-mercaptoethyl)guanidine；N-cyano-N'-methyl-N''-(2-mercaptoethyl)guanidine；1-cyano-2-methyl-3-(2-sulfanylethyl)guanidine
• CAS: 61085-25-4；76181-72-1
• 化学式: C₅H₁₀N₄S
• 分子量: 158.227
• InChiKey: ZORWZOOZJGMSTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  61.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-氰基-N'-(2-巯基乙基)-N''-甲基胍 生成 1-cyano-3-[2-[(2Z)-2-hydroxyimino-3-oxobutyl]sulfanylethyl]-2-methylguanidine
  参考文献：
  名称：

  摘要：

  DOI：
• 作为产物：
  描述：

  西咪替丁EP杂质H 以69%的产率得到
  参考文献：
  名称：

  ISITOKU, TAKEHSI;KIXARA, NORIAKI;KODZATO, AJITIRO;KATO, XODZI

  摘要：

  DOI：

文献信息

• Aminoalkyl furan derivatives
  申请人：Allen & Hanburys Limited

  公开号：US04128658A1

  公开（公告）日：1978-12-05

  Compounds of the general formula I: ##STR1## and physiologically acceptable salts thereof and N-oxides and hydrates, in which R.sub.1 and R.sub.2 which may be the same or different represent hydrogen, lower alkyl, cycloalkyl, lower alkenyl, aralkyl or lower alkyl interrupted by an oxygen atom or a group ##STR2## in which R.sub.4 represents hydrogen or lower alkyl or R.sub.1 and R.sub.2 may, together with the nitrogen atom to which they are attached, form a heterocyclic ring which may contain other heteroatoms selected from O and ##STR3## R.sub.3 is hydrogen, lower alkyl, lower alkenyl or alkoxyalkyl; X is --CH.sub.2 --, O or S; Y represents .dbd. S, .dbd. O, .dbd. NR.sub.5 or .dbd. CHR.sub.6 ; Alk denotes a straight or branched alkylene chain of 1 to 6 carbon atoms; R.sub.5 is H, nitro, cyano, lower alkyl, aryl, alkylsulphonyl, or arylsulphonyl; R.sub.6 represents nitro, arylsulphonyl or alkylsulphonyl; M is an integer from 2 to 4; and N is 1 or 2; or when X .dbd. S, or --CH.sub.2 --, n is zero, 1 or 2. These compounds have H.sub.2 -antagonist activity. Intermediates in the production thereof are also provided.

  通式I的化合物：##STR1##及其生理上可接受的盐和N-氧化物和水合物，其中R.sub.1和R.sub.2可以相同也可以不同，代表氢、较低的烷基、环烷基、较低的烯基、芳基烷基或被氧原子或基团##STR2##中断的较低烷基，其中R.sub.4代表氢或较低烷基或R.sub.1和R.sub.2可以与它们连接的氮原子一起形成可能包含其他杂原子O和##STR3##的杂环环，R.sub.3是氢、较低烷基、较低烯基或烷氧基烷基；X是--CH.sub.2--、O或S；Y代表.dbd. S、.dbd. O、.dbd. NR.sub.5或.dbd. CHR.sub.6；Alk表示由1到6个碳原子的直链或支链烷基链；R.sub.5是H、硝基、氰基、较低烷基、芳基、烷基磺酰基或芳基磺酰基；R.sub.6代表硝基、芳基磺酰基或烷基磺酰基；M是从2到4的整数；N是1或2；或当X.dbd.S或--CH.sub.2--时，n为零、1或2。这些化合物具有H.sub.2-拮抗活性。还提供了其生产中间体。
• Unexpected O ? S and N ? S alkyl transfer reactions in the reaction of 3-alkyl-2-(N-cyanoimino)thiazolidines with sodium alkoxides: a new synthesis of cimetidine
  作者：Chuzo Iwata、Michitaro Fujimoto、Mayumi Watanabe、Tetsuya Kawakami、Yumi Nakamoto、Masatoshi Sakae、Masanori Katsurada、Takeshi Imanishi、Tetsuaki Tanaka

  DOI：10.1039/c39920001379

  日期：——

  Unexpected O → S and N → S alkyl transfer reactions were observed in the reaction of 3-alkyl-2-(N-cyanoimino)thiazolidines with sodium alkoxides, and a new synthetic method for cimetidine was developed using the N → S alkyl transfer reaction as a key step.

  在 3-烷基-2-（N-氰基亚胺）噻唑烷与烷氧基化钠的反应中，观察到了意想不到的 O - S 和 N - S 烷基转移反应，并以 N - S 烷基转移反应为关键步骤，开发出了一种新的西咪替丁合成方法。
• Synthesis of N,N′-Disubstituted N″-2-(2-Quinolinylmethylthio)ethylguanidines as Potential Anticancer Agents
  作者：William O. Foyex、Seung Ho An、Timothy J. Maher

  DOI：10.1002/jps.2600730838

  日期：1984.8

  A simple method for obtaining the title compounds was found in the alkaline rearrangement of S-2-aminoethylisothiouronium salts, which were obtained from the condensation of thiourea or substituted thioureas with 2-bromoethylamine hydrobromide. No activity was found for the substituted guanidines against P388 lymphocytic leukemia in mice, or as H2-receptor antagonists.

  在S-2-氨基乙基异硫脲盐的碱重排中发现了一种简单的获得标题化合物的方法，该盐是从硫脲或取代的硫脲与2-溴乙胺氢溴酸盐的缩合反应中获得的。没有发现取代的胍抗小鼠或作为H2受体拮抗剂的P388淋巴细胞白血病的活性。
• Synthesis of Cimetidine
  作者：Pekka Kairisalo、Erkki Honkanen

  DOI：10.1002/ardp.19833160807

  日期：——

  A simple and economical synthesis of cimetidine is described. It is based on the reaction of 4‐halomethyl‐5‐methylimidazole with N‐cyano‐N′‐methyl‐N″‐(2‐mercaptoethyl)guanidine in water‐ethanol at pH 9.0 ± 0.3. Pure crystalline cimetidine is obtained in about 75% yield.

  描述了一种简单且经济的西咪替丁合成方法。它基于 4-卤甲基-5-甲基咪唑与 N-氰基-N'-甲基-N″-(2-巯基乙基)胍在水-乙醇中在pH 9.0 ± 0.3 中的反应。以约75%的产率获得纯结晶西咪替丁。
• Process for preparing heterocyclicalkylthioalkyl-N-cyanoguanidines
  申请人：Smith Kline & French Laboratories Limited

  公开号：US04013678A1

  公开（公告）日：1977-03-22

  Process for preparing heterocyclicalkylthioalkyl-N-cyanoguanidines and thioureas by treating a heterocyclicalkyl derivative with a mercaptoalkyl-N-cyanoguanidine or thiourea. Two specific products are N-cyano-N'-methyl-N"-[2-((5-methyl-4-imidazolyl)methylthio)ethyl]guanidine and N-methyl-N'-[2-((5-methyl-4-imidazolyl)methylthio)ethyl]thiourea, both useful as histamine H.sub.2 -antagonists.

  通过用巯基烷基-N-氰基脲或硫脲处理杂环烷基衍生物来制备杂环烷基硫基-N-氰基脲和硫脲的过程。两种具体产品是N-氰基-N'-甲基-N"-[2-((5-甲基-4-咪唑基)甲硫基)乙基]脲和N-甲基-N'-[2-((5-甲基-4-咪唑基)甲硫基)乙基]硫脲，均可用作组胺H.sub.2-拮抗剂。