N-butyl-S-methyl-isothiourea; hydriodide | 925-67-7

• 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-butyl-S-methyl-isothiourea; hydriodide
• 英文别名: N-Butyl-S-methyl-isothioharnstoff; Hydrojodid；1-butyl-2-methylisothiourea hydroiodide；methyl N'-butylcarbamimidothioate;hydroiodide
• CAS: 925-67-7
• 化学式: C₆H₁₄N₂S*HI
• 分子量: 274.169
• InChiKey: RUDKKVNUTJIBSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.08
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  63.7
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-butyl-S-methyl-isothiourea; hydriodide 、 N,N-二乙基乙二胺 以 乙醇 为溶剂， 生成 N-Butyl-N'-(2-diethylamino-ethyl)-guanidin
  参考文献：
  名称：

  交感神经系统阻滞剂。胍基衍生物和相关化合物。

  摘要：

  DOI：

  10.1021/jm00339a013
• 作为产物：
  描述：

  丁基异硫氰酸酯 在 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 反应 3.5h， 生成 N-butyl-S-methyl-isothiourea; hydriodide
  参考文献：
  名称：

  Potent gonadotropin releasing hormone antagonists with low histamine-releasing activity

  摘要：

  The incorporation of Arg residues into position 6 of gonadotropin releasing hormone antagonists had resulted in compounds with increased in vivo potency but also made these analogues potent mast cell degranulators. We have focused on the substitution of position 8 by hArg(R)2 (N(G),N(G)'-dialkylhomoarginine) substitutions, based on the hypotheses that the Arg-Pro sequence is of major importance for this side effect and that shielding of the charge may be an effective way to block degranulation. Analogues in four series were evaluated: (A) [N-Ac-D-Nal(2)1,D-pCl-Phe2,D-Pal-(3)3,6,Arg5,hArg(R)2(8),D-Ala10]GnRH, (B) [N-Ac-D-Nal(2)1,D-pCl-Phe2,D-Pal(3)3,6,hArg(R)2(5,8),D-Ala10]-GnRH, (C) [N-Ac-D-Nal(2)1,D-pCl-Phe2,D-Pal(3)3,6,hArg(R)28,D-Ala10]GnRH, (D) [N-Ac-D-Nal(2)1,D-pCl-Phe2,D-Pal(3)3,D-hArg(R)2(6),hArg(R)2(8),D-Ala10]GnRH. Although substitution by hArg(Et)2, hArg(Bu), hArg(CH2)3, and hArg(CH2CF3)2 was tested, in each series the hArg(Et)2 residue was superior. Two compounds were considered for clinical evaluation: [N-Ac-D-Nal(2)1,D-pCl-Phe2,D-Pal(3)3,6,hArg(Et)2(8),D-Ala10]GnRH and [N-AC-D-Nal(2)1,D-pCl-Phe2,D-Pal(3)3,D-hArg(Et)26,hArg-(Et)28,D-Ala10]GnRH (ganirelix acetate). These compounds had high potency for ovulation suppression and low histamine-releasing potency in vitro (ED50 = 0.6,0.29 mug/rat and EC50 = 196, 13 mug/mL, respectively). Ganirelix is currently in Phase II clinical trials and appears to be the most potent GnRH antagonist tested in humans (based upon ED50 for 24-h suppression of testosterone levels).

  DOI：

  10.1021/jm00099a023

文献信息

• Substituted guanidinedicarbonyl derivatives
  申请人：American Cyanamid Company

  公开号：US04977189A1

  公开（公告）日：1990-12-11

  This disclosure describes novel substituted guanidinedicarbonyl derivatives which possess anxiolytic activity and are also useful as agents for the treatment of cognitive and related neural behavioral problems in mammals.

  这份披露描述了新型的取代胍二羰基衍生物，具有抗焦虑活性，并且也可作为治疗哺乳动物认知和相关神经行为问题的药物。
• Reduction of Nitroguanidine. V. The Synthesis of (a) α-Methyl-, (b) α-Ethyl-, (c) α-n-Butyl-γ-aminoguanidine¹
  作者：G. W. Kirsten、G. B. L. Smith

  DOI：10.1021/ja01296a036

  日期：1936.5
• US4056527A
  申请人：——

  公开号：US4056527A

  公开（公告）日：1977-11-01
• US4977189A
  申请人：——

  公开号：US4977189A

  公开（公告）日：1990-12-11
• Sympathetic Nervous System Blocking Agents. Derivatives of Guanidine and Related Compounds¹
  作者：James H. Short、Ursula Biermacher、Daniel A. Dunnigan、Thomas D. Leth

  DOI：10.1021/jm00339a013

  日期：1963.5