Boc-Gln-Asn-Cys(Bzl)-Pro-Leu-Gly-N(CH3)2 | 73631-32-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Boc-Gln-Asn-Cys(Bzl)-Pro-Leu-Gly-N(CH3)2
• CAS: 73631-32-0
• 化学式: C₃₉H₆₁N₉O₁₀S
• 分子量: 848.034
• InChiKey: CIPRRARKIOWNHA-ZIUUJSQJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.35
• 重原子数：
  59.0
• 可旋转键数：
  22.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  281.53
• 氢给体数：
  7.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  Boc-Gln-Asn-Cys(Bzl)-Pro-Leu-Gly-N(CH3)2 、 三氟乙酸 生成 (S)-1-{(R)-2-[(S)-2-((S)-2-Amino-4-carbamoyl-butyrylamino)-3-carbamoyl-propionylamino]-3-benzylsulfanyl-propionyl}-pyrrolidine-2-carboxylic acid [(S)-1-(dimethylcarbamoylmethyl-carbamoyl)-3-methyl-butyl]-amide; compound with trifluoro-acetic acid
  参考文献：
  名称：

  Effect of changing the COOH-terminal amide group present in the hydrophilic cluster of oxytocin to dimethylamide

  摘要：

  Oxytocinoic acid dimethylamide was synthesized by stepwise solution techniques as part of an ongoing evaluation of the effects on the biological activity of oxytocin caused by individually changing the groups that comprises the hydrophilic surface of the hormone to more hydrophobic and more bulky groups. The analogue exhibited approximately 3% of the potency of oxytocin in the in vitro uterotonic assay. In addition, it possesses potencies of less than 0.07, less than 0.01, and 0.096 unit/mg in the avian vasodepressor, rat pressor, and rat antidiuretic assays, respectively. In the in vitro uterotonic assay, oxytocinoic acid dimethylamide showed a reduced affinity for the oxytocin receptor, a nonparallel dose-response relationship, and most importantly a reduced intrinsic activity as compared to oxytocin. The results suggest that the replacement of the protons of the primary carboxyamide of Gly9-NH2 of oxytocin by methyl groups displaces the active elements from the orientation for obtaining maximal intrinsic activity in the isolated rat uterus.

  DOI：

  10.1021/jm00180a026
• 作为产物：
  描述：

  2-叔丁氧羰基氨基-4-氨基甲酰基丁酸 4-硝基苯酯 、 (S)-2-Amino-N¹-((R)-1-benzylsulfanylmethyl-2-{(S)-2-[(S)-1-(dimethylcarbamoylmethyl-carbamoyl)-3-methyl-butylcarbamoyl]-pyrrolidin-1-yl}-2-oxo-ethyl)-succinamide; compound with trifluoro-acetic acid 在 N-甲基吗啉 作用下， 以74%的产率得到Boc-Gln-Asn-Cys(Bzl)-Pro-Leu-Gly-N(CH3)2
  参考文献：
  名称：

  Effect of changing the COOH-terminal amide group present in the hydrophilic cluster of oxytocin to dimethylamide

  摘要：

  Oxytocinoic acid dimethylamide was synthesized by stepwise solution techniques as part of an ongoing evaluation of the effects on the biological activity of oxytocin caused by individually changing the groups that comprises the hydrophilic surface of the hormone to more hydrophobic and more bulky groups. The analogue exhibited approximately 3% of the potency of oxytocin in the in vitro uterotonic assay. In addition, it possesses potencies of less than 0.07, less than 0.01, and 0.096 unit/mg in the avian vasodepressor, rat pressor, and rat antidiuretic assays, respectively. In the in vitro uterotonic assay, oxytocinoic acid dimethylamide showed a reduced affinity for the oxytocin receptor, a nonparallel dose-response relationship, and most importantly a reduced intrinsic activity as compared to oxytocin. The results suggest that the replacement of the protons of the primary carboxyamide of Gly9-NH2 of oxytocin by methyl groups displaces the active elements from the orientation for obtaining maximal intrinsic activity in the isolated rat uterus.

  DOI：

  10.1021/jm00180a026