(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-2-propan-2-ylsulfanylacetic acid | 937389-77-0

• 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: (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-2-propan-2-ylsulfanylacetic acid
• CAS: 937389-77-0
• 化学式: C₁₀H₁₉NO₄S
• 分子量: 249.331
• InChiKey: IDULSBCWTXSUII-ZETCQYMHSA-N

物化性质

• 沸点：
  366.4±37.0 °C(Predicted)
• 密度：
  1.158±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-2-propan-2-ylsulfanylacetic acid 、 乙酸酐 、 Boc-3-(2-萘基)-D-丙氨酸 、 Boc-4-(Fmoc-氨基)-L-苯丙氨酸 、 Boc-D-4Aph(Fmoc)-OH 、 alkaline earth salt of/the/ methylsulfuric acid 、 alkaline earth salt of/the/ methylsulfuric acid 生成 (2S)-1-[(2S)-2-[[(2S)-2-[[(2R)-2-[[(2S)-2-[[(2S)-2-[[(2R)-2-[[(2R)-3-(4-chlorophenyl)-1-hydroxy-2-[[(2R)-1-hydroxy-2-(1-hydroxyethylideneamino)-3-naphthalen-2-ylpropylidene]amino]propylidene]amino]-1-hydroxy-3-pyridin-3-ylpropylidene]amino]-1,3-dihydroxypropylidene]amino]-1-hydroxy-3-[4-(1-hydroxyethylideneamino)phenyl]propylidene]amino]-1-hydroxy-3-[4-(1-hydroxyethylideneamino)phenyl]propylidene]amino]-1-hydroxy-2-propan-2-ylsulfanylethylidene]amino]-6-(propan-2-ylamino)hexanoyl]-N-[(2R)-1-hydroxy-1-iminopropan-2-yl]pyrrolidine-2-carboximidic acid
  参考文献：
  名称：

  Structure−Activity Relationship Studies of Gonadotropin-Releasing Hormone Antagonists Containing S-Aryl/Alkyl Norcysteines and Their Oxidized Derivatives

  摘要：

  A series of acyline analogues incorporating L- and D-isomers of S-arylated/alkylated norcysteines [Ncy(R), where R is 2-naphthyl, methyl, and isopropyl] at positions 1, 4, 7, and 10 were synthesized. Some of these analogues were mono- and dioxidized to sulfoxides and sulfones. All of the analogues of acyline were screened for the antagonism of the GnRH-induced response in a reporter gene assay in HEK-293 cells expressing the human GnRH receptor. Nine of the analogues (9, 11, 15, 16, 17, 19, 20 21, and 22) had antagonistic potency (IC50 < 2 nM) similar to that of acyline (IC50 = 0.52 nM) in this assay. Selected analogues (9, 11, 15, 16, 19, and 21) were tested in vitro for their antagonism at the rat GnRH-R in a reporter gene assay as well as in an in vivo intact male rat assay. Analogues 9 and 15 were the most potent in suppressing testosterone levels.

  DOI：

  10.1021/jm0613931
• 作为产物：
  描述：

  氨基甲酸叔丁酯 在 papain 、 1,4-二巯基-2,3-丁二醇 对甲苯磺酸 、 柠檬酸 作用下， 以 甲醇 、 phosphate buffer 、 正己烷 、 丙酮 、 甲苯 、 乙腈 、 苯 为溶剂， 反应 23.75h， 生成 (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-2-propan-2-ylsulfanylacetic acid
  参考文献：
  名称：

  Structure−Activity Relationship Studies of Gonadotropin-Releasing Hormone Antagonists Containing S-Aryl/Alkyl Norcysteines and Their Oxidized Derivatives

  摘要：

  A series of acyline analogues incorporating L- and D-isomers of S-arylated/alkylated norcysteines [Ncy(R), where R is 2-naphthyl, methyl, and isopropyl] at positions 1, 4, 7, and 10 were synthesized. Some of these analogues were mono- and dioxidized to sulfoxides and sulfones. All of the analogues of acyline were screened for the antagonism of the GnRH-induced response in a reporter gene assay in HEK-293 cells expressing the human GnRH receptor. Nine of the analogues (9, 11, 15, 16, 17, 19, 20 21, and 22) had antagonistic potency (IC50 < 2 nM) similar to that of acyline (IC50 = 0.52 nM) in this assay. Selected analogues (9, 11, 15, 16, 19, and 21) were tested in vitro for their antagonism at the rat GnRH-R in a reporter gene assay as well as in an in vivo intact male rat assay. Analogues 9 and 15 were the most potent in suppressing testosterone levels.

  DOI：

  10.1021/jm0613931