3-O-methyl-α-L-rhamnopyranose | 78185-80-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-methyl-α-L-rhamnopyranose
• 英文别名: 3-O-methyl-α-L-rhamnose；3-O-methyl rhamnopyranose；α-L-acofrioside；L-acofriose；O³-methyl-L-6-deoxy-mannose；O³-methyl-α-L-6-deoxy-mannopyranose；6-deoxy-3-O-methyl-alpha-L-mannopyranose；(2R,3R,4R,5S,6S)-4-methoxy-6-methyloxane-2,3,5-triol
• CAS: 78185-80-5
• 化学式: C₇H₁₄O₅
• 分子量: 178.185
• InChiKey: OEKPKBBXXDGXNB-PAMBMQIZSA-N

物化性质

• 沸点：
  328.1±42.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  quercetin 3-O-(3-O-methyl-α-L-rhamnopyranoside) 在 硫酸 、 水 作用下， 反应 1.0h， 生成 3-O-methyl-α-L-rhamnopyranose 、 槲皮素
  参考文献：
  名称：

  New Hedgehog/GLI signaling inhibitors from Excoecaria agallocha

  摘要：

  The inhibition of the Hedgehog (Hh) signaling pathway has emerged as an anti-cancer strategy. Three flavonoid glycosides including 2 new compounds (1-2) were isolated from Excoecaria agallocha as Hedgehog/GLI1-mediated transcriptional inhibitors and exhibited cytotoxicity against human pancreatic (PANC1) and prostate (DU145) cancer cells. Our data revealed that compound 1 clearly inhibited the expression of GLI-related proteins (PTCH and BCL-2) and blocked the translocation of GLI1 transcription factors into the nucleus in PANC1. Deleting the Smoothened (Smo) function in PANC1 treated with 1 led to downregulation of the mRNA expression of Ptch. This study describes the first Hh signaling inhibitor which blocks GLI1 movement into the nucleus without interfering with Smo. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.11.126

文献信息

• Yamauchi, Tatsuo; Abe, Fumiko; Wan, Alfred S.C., Chemical and pharmaceutical bulletin, 1987, vol. 35, # 7, p. 2744 - 2749
  作者：Yamauchi, Tatsuo、Abe, Fumiko、Wan, Alfred S.C.

  DOI：——

  日期：——
• WO2023/168520
  申请人：——

  公开号：——

  公开（公告）日：——
• New Hedgehog/GLI signaling inhibitors from Excoecaria agallocha
  作者：Yusnita Rifai、Midori A. Arai、Samir K. Sadhu、Firoj Ahmed、Masami Ishibashi

  DOI：10.1016/j.bmcl.2010.11.126

  日期：2011.1

  The inhibition of the Hedgehog (Hh) signaling pathway has emerged as an anti-cancer strategy. Three flavonoid glycosides including 2 new compounds (1-2) were isolated from Excoecaria agallocha as Hedgehog/GLI1-mediated transcriptional inhibitors and exhibited cytotoxicity against human pancreatic (PANC1) and prostate (DU145) cancer cells. Our data revealed that compound 1 clearly inhibited the expression of GLI-related proteins (PTCH and BCL-2) and blocked the translocation of GLI1 transcription factors into the nucleus in PANC1. Deleting the Smoothened (Smo) function in PANC1 treated with 1 led to downregulation of the mRNA expression of Ptch. This study describes the first Hh signaling inhibitor which blocks GLI1 movement into the nucleus without interfering with Smo. (C) 2010 Elsevier Ltd. All rights reserved.