S-Methyl-N-butyl-isothioharnstoff | 100319-25-3

• 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: S-Methyl-N-butyl-isothioharnstoff
• 英文别名: methyl N'-butylcarbamimidothioate
• CAS: 100319-25-3
• 化学式: C₆H₁₄N₂S
• mdl: MFCD19217512
• 分子量: 146.257
• InChiKey: WLIDQCHXBFDAKG-UHFFFAOYSA-N

物化性质

• 沸点：
  189.9±23.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.833
• 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：

  S-Methyl-N-butyl-isothioharnstoff 生成 N-Butyl-N'-hydroxy-guanidin-O-sulfonsaeure
  参考文献：
  名称：

  Hessing,A.; Peppmoeller,R., Zeitschrift fur Naturforschung. Teil B: Chemie, Biochemie, Biophysik, Biologie, 1967, vol. 22, p. 820 - 824

  摘要：

  DOI：
• 作为产物：
  描述：

  正丁基硫脲 、 碘甲烷 以 乙醇 为溶剂， 生成 S-Methyl-N-butyl-isothioharnstoff
  参考文献：
  名称：

  Isothiuronium, Alkylthioöxazolinium, and Alkylthiothiazolinium Picrates¹

  摘要：

  DOI：

  10.1021/jo01060a020

文献信息

• 1-ARYLSULPHONYL-3-<i>n</i>-BUTYL-2-METHYL-2-THIOPSEUDOUREAS
  作者：Stanley O. Winthrop、Gregory Gavin

  DOI：10.1139/v58-104

  日期：1958.4.1

  not available

  不可用。
• Potent gonadotropin releasing hormone antagonists with low histamine-releasing activity
  作者：John J. Nestor、Ram Tahilramani、Teresa L. Ho、Jessie C. Goodpasture、Brian H. Vickery、Pierre Ferrandon

  DOI：10.1021/jm00099a023

  日期：1992.10

  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).
• US3995050A
  申请人：——

  公开号：US3995050A

  公开（公告）日：1976-11-30
• 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
• Hessing,A.; Peppmoeller,R., Zeitschrift fur Naturforschung. Teil B: Chemie, Biochemie, Biophysik, Biologie, 1967, vol. 22, p. 820 - 824
  作者：Hessing,A.、Peppmoeller,R.

  DOI：——

  日期：——