(3R,6S,9S,12S,15S,18R)-15-(2-amino-2-oxoethyl)-N-[(2S)-1-amino-1-oxopropan-2-yl]-18-[[(2S)-2,6-diaminohexanoyl]amino]-6,12-bis[(1R)-1-hydroxyethyl]-9-methyl-5,8,11,14,17-pentaoxo-1,20-dithia-4,7,10,13,16-pentazacyclotricosane-3-carboxamide | 1372190-63-0

• 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: (3R,6S,9S,12S,15S,18R)-15-(2-amino-2-oxoethyl)-N-[(2S)-1-amino-1-oxopropan-2-yl]-18-[[(2S)-2,6-diaminohexanoyl]amino]-6,12-bis[(1R)-1-hydroxyethyl]-9-methyl-5,8,11,14,17-pentaoxo-1,20-dithia-4,7,10,13,16-pentazacyclotricosane-3-carboxamide
• CAS: 1372190-63-0
• 化学式: C₃₃H₅₉N₁₁O₁₁S₂
• 分子量: 850.031
• InChiKey: OQQWMRKLFMGFEJ-JNSUXVKTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.3
• 重原子数：
  57
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  433
• 氢给体数：
  13
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  H-Lys-Cys-Asn-Thr-Ala-Thr-Cys-Ala-NH2 、 1,3-二溴丙烷 在 三(2-羰基乙基)磷盐酸盐 作用下， 以 水 、 乙腈 为溶剂， 反应 96.0h， 以0.5 mg的产率得到(3R,6S,9S,12S,15S,18R)-15-(2-amino-2-oxoethyl)-N-[(2S)-1-amino-1-oxopropan-2-yl]-18-[[(2S)-2,6-diaminohexanoyl]amino]-6,12-bis[(1R)-1-hydroxyethyl]-9-methyl-5,8,11,14,17-pentaoxo-1,20-dithia-4,7,10,13,16-pentazacyclotricosane-3-carboxamide
  参考文献：
  名称：

  Synthesis and evaluation of disulfide bond mimetics of amylin-(1–8) as agents to treat osteoporosis

  摘要：

  Osteoporotic fracture is a significant public health problem, resulting in fractures in >50% of women and in almost one third of men age 65 and older. Most of the existing therapies act by slowing bone loss, through inhibiting the action of bone resorbing cells. However, more substantial reductions of fracture numbers will only result from treatments that can rebuild bone. Our own animal studies demonstrated the anabolic potential of the small but unstable octapeptide fragment of amylin-(1-37), namely amylin-(1-8) containing one disulfide bridge (Cys/2 and Cys/7) [Am. J. Physiol. Endocrinol. Metab. 2000, 279, E730]. Herein, we describe the synthesis of amylin-(1-8) octapeptide and seven analogues thereof wherein the disulfide bridge is modified either via insertion of different linkers or bridges of a different nature in order to improve the stability and/or bone anabolic activity of the parent peptide. The peptide analogues were screened for proliferative activity in primary foetal rat bone-forming cells or osteoblasts at physiological concentrations. One such analogue showed promising biological activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.02.030