N-ethyl-S-methyl-isothiourea | 44595-80-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 异硫脲类
• 英文名称: N-ethyl-S-methyl-isothiourea
• 英文别名: 1-Ethyl-2-methyl-isothiourea
• CAS: 44595-80-4
• 化学式: C₄H₁₀N₂S
• mdl: MFCD20617136
• 分子量: 118.2
• InChiKey: HRDFVQLHRAQAKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  63.7
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  二碳酸二叔丁酯 、 N-ethyl-S-methyl-isothiourea 在 碳酸氢钠 作用下， 以 1,4-二氧六环 为溶剂， 生成 N-ethyl-N'-t-butyloxycarbonyl-S-methylisothiourea
  参考文献：
  名称：

  A General Procedure for Synthesis ofN^G-Alkyl, andN^G-Aryl-L-Arginines as Potential Nitric Oxide Synthase inhibitors

  摘要：

  AbstractA general procedure for the synthesis of NG‐alkyl, and NG‐aryl‐L‐arginines with relatively high overall yield is reported. The key step involved the coupling of protected L‐ornithine 4 with isothiourea 7 to give the fully protected NG‐aryl‐L‐arginine derivative 8. Subsequent deprotection of 8 in acidic condition provided the final target compound 9 with an overall yield of more than 80%.

  DOI：

  10.1002/jccs.199800083
• 作为产物：
  描述：

  乙基硫脲 、 碘甲烷 以 丙酮 为溶剂， 反应 1.0h， 生成 N-ethyl-S-methyl-isothiourea
  参考文献：
  名称：

  A General Procedure for Synthesis ofN^G-Alkyl, andN^G-Aryl-L-Arginines as Potential Nitric Oxide Synthase inhibitors

  摘要：

  AbstractA general procedure for the synthesis of NG‐alkyl, and NG‐aryl‐L‐arginines with relatively high overall yield is reported. The key step involved the coupling of protected L‐ornithine 4 with isothiourea 7 to give the fully protected NG‐aryl‐L‐arginine derivative 8. Subsequent deprotection of 8 in acidic condition provided the final target compound 9 with an overall yield of more than 80%.

  DOI：

  10.1002/jccs.199800083

文献信息

• 4,5,6,7-Tetrahydroimidazo-[4,5-c]-pyridine derivatives
  申请人：Societa' Farmaceutici Italia S.p.A.

  公开号：US04141899A1

  公开（公告）日：1979-02-27

  New 4,5,6,7-tetrahydroimidazo-[4,5-c]-pyridine derivatives are disclosed, and more particularly derivatives of Formula I ##STR1## where R.sub.1 is hydrogen or an alkyl having from 1 to 4 carbon atoms; R.sub.2 is hydrogen, an alkyl having from 1 to 4 carbon atoms, a cycloalkyl having from 3 to 6 carbon atoms, phenyl or a heterocycle; R.sub.3 is hydrogen, a saturated or unsaturated straight or branched alkyl having from 1 to 6 carbon atoms, a cycloalkyl having from 3 to 6 carbon atoms, benzoyl or phenyl; and X is O, S or NR.sub.4 where R.sub.4 is hydrogen, an alkyl having from 1 to 4 carbon atoms, cyano, amino, nitro or acylamino; Or pharmaceutically acceptable acid addition salts thereof. Also disclosed is a process of preparing these compounds which comprises condensing an appropriate 4,5,6,7-tetrahydroimidazo-[4,5-c]-pyridine with an appropriate alkyl isocyanate, alkyl isothiocyanate or substituted S-methyl thiourea, preferably in a solvent such as ethanol, acetonitrile or dioxane, usually under reflux for from 4 to 12 hours. The products can be isolated by crystallization as free bases or as salts of pharmaceutically acceptable acids. The new compounds have proved to be well tolerated and to inhibit both the number of experimental ulcers and the gastric secretion in experimental animals. Thus, they should prove useful in the therapy of gastric and duodenal ulcers in man.

  本文揭示了新的4,5,6,7-四氢咪唑[4,5-c]-吡啶衍生物，更具体地是公式I的衍生物：##STR1## 其中R.sub.1为氢或具有1至4个碳原子的烷基；R.sub.2为氢、具有1至4个碳原子的烷基、具有3至6个碳原子的环烷基、苯基或杂环基；R.sub.3为氢、具有1至6个碳原子的饱和或不饱和直链或支链烷基、具有3至6个碳原子的环烷基、苯甲酰基或苯基；X为O、S或NR.sub.4，其中R.sub.4为氢、具有1至4个碳原子的烷基、氰基、氨基、硝基或酰胺基；或其药学上可接受的酸盐。还揭示了制备这些化合物的过程，包括将适当的4,5,6,7-四氢咪唑[4,5-c]-吡啶与适当的烷基异氰酸酯、烷基异硫氰酸酯或取代的S-甲基硫脲缩合，通常在乙醇、乙腈或二恶英等溶剂中回流4至12小时。产物可以通过结晶作为自由碱基或药学上可接受的酸盐分离。新化合物被证明耐受性良好，并且在实验动物中抑制溃疡数量和胃分泌物。因此，它们应该在治疗人类胃十二指肠溃疡方面证明有用。
• Schenck; Kirchhof, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1926, vol. 158, p. 94
  作者：Schenck、Kirchhof

  DOI：——

  日期：——
• A Facile Route to Cyclic and Acyclic Alkyl-Arginines
  作者：Kevin J. Kennedy、Tiberiu L. Simandan、Thomas A. Dix

  DOI：10.1080/00397919808005947

  日期：1998.2

  Treatment of commercially available alkyl and cycloalkyl thioureas with methyl iodide provides the corresponding S-alkylisothiouronium iodide which reacts directly with ornithine to yield the title compounds.
• Isothiuronium, Alkylthioöxazolinium, and Alkylthiothiazolinium Picrates¹
  作者：LOUIS LONG、RICHARD C. CLAPP、FRANK H. BISSETT、TORSTEN HASSELSTROM

  DOI：10.1021/jo01060a020

  日期：1961.1
• Synthesis of cyclic and acyclic Nα-methyl-Nω-alkyl-l-arginine analogues
  作者：Kyle P. Kokko、H. Brooks Hooper、Thomas A. Dix

  DOI：10.1016/j.tetlet.2004.01.047

  日期：2004.3

  A series of Nalpha-methyl-alkyl-L-arginine (Arg) analogues have been synthesized from inexpensive, commercially available starting rnaterials. These analogues, once incorporated into pharmaceutically relevant peptides, are expected to increase binding affinity, receptor selectivity, lipophificity, and stability Lis demonstrated With analogues of similar design and Structure. (C) 2001 Published by Elsevier Ltd.