O-ethyl-4-<(2',3',4'-tri-O-acetyl-α-L-rhamnopyranosyloxy)benzyl>thiocarbamate (Z) | 147821-50-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-ethyl-4-<(2',3',4'-tri-O-acetyl-α-L-rhamnopyranosyloxy)benzyl>thiocarbamate (Z)
• 英文别名: [(2S,3S,4R,5R,6S)-4,5-diacetyloxy-6-[4-[(ethoxycarbothioylamino)methyl]phenoxy]-2-methyloxan-3-yl] acetate
• CAS: 147821-50-9
• 化学式: C₂₂H₂₉NO₉S
• 分子量: 483.54
• InChiKey: WYFYRQBBNVSDHV-CDEOHPBMSA-N

物化性质

• 沸点：
  549.4±60.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  151
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  O-ethyl-4-<(2',3',4'-tri-O-acetyl-α-L-rhamnopyranosyloxy)benzyl>thiocarbamate (Z) 在 甲醇 、 sodium methylate 作用下， 反应 0.75h， 以95%的产率得到O-乙基[[4-(3,4,5-三羟基-6-甲基四氢吡喃-2-基)氧基苯基]甲基氨基]硫代甲酸酯
  参考文献：
  名称：

  Synthesis of active principles from the leaves of Moringa oleifera using S-pent-4-enyl thioglycosides

  摘要：

  alpha-L-Rhamnosides of 4-hydroxy-benzyl compounds with nitrile, carbamate, and thiocarbamate groups occurring in Moringa oleifera leaf extracts and the alpha-L-rhamnoside of anisaldehyde derivatives were synthesised. Electrophilic activation of S-pent-4-enyl thiorhamnosides was applied for the construction of glycosidic linkages. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00223-7
• 作为产物：
  描述：

  4-(烯丙氧基)苯甲腈 在 palladium diacetate 、 lithium aluminium tetrahydride 、 甲酸 、 三氟化硼乙醚 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 59.17h， 生成 O-ethyl-4-<(2',3',4'-tri-O-acetyl-α-L-rhamnopyranosyloxy)benzyl>thiocarbamate (Z)
  参考文献：
  名称：

  Synthesis of active principles from the leaves of Moringa oleifera using S-pent-4-enyl thioglycosides

  摘要：

  alpha-L-Rhamnosides of 4-hydroxy-benzyl compounds with nitrile, carbamate, and thiocarbamate groups occurring in Moringa oleifera leaf extracts and the alpha-L-rhamnoside of anisaldehyde derivatives were synthesised. Electrophilic activation of S-pent-4-enyl thiorhamnosides was applied for the construction of glycosidic linkages. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00223-7

文献信息

• Niaziminin, a Thiocarbamate from the Leaves of<i>Moringa oleifera</i>, Holds a Strict Structural Requirement for Inhibition of Tumor-Promoter-Induced Epstein-Barr Virus Activation
  作者：Akira Murakami、Yumi Kitazono、Suratwadee Jiwajinda、Koichi Koshimizu、Hajime Ohigashi

  DOI：10.1055/s-2006-957442

  日期：1998.5

  Three known thiocarbamate (TC)- and isothiocyanate (ITC)-related compounds have been isolated from the leaves of Moringa oleifera, a traditional herb in southeast Asia, as inhibitors of tumor promoter teleocidin B-4-induced Epstein-Barr virus (EBV) activation in Raji cells. Interestingly, only niaziminin among 10 TCs including 8 synthetic ones showed considerable inhibition against EBV activation. The structure-activity relationships indicated that the presence of an acetoxy group at the 4′-position of niaziminin is important and indispensable for inhibition. On the other hand, among the ITC-related compounds, naturally occurring 4-[(4′-O-acetyl-α-L-rhamnosyloxy)benzyl]ITC and commercially available allyl- and benzyl-ITC significantly inhibited activation, suggesting that the isothiocyano group is a critical structural factor for activity.

  从东南亚传统草药辣木的叶子中分离出三种已知的硫代氨基甲酸盐（TC）和异硫氰酸盐（ITC）相关化合物，它们被鉴定为肿瘤促进剂大田软海绵素B-4诱导的Raji细胞中的爱泼斯坦-巴尔病毒（EBV）激活的抑制剂。有趣的是，在包括8种合成化合物在内的10种TC中，只有niaziminin表现出对EBV激活的显著抑制作用。结构-活性关系研究表明，niaziminin在4′-位置上的乙酰氧基对于抑制作用至关重要且不可或缺。另一方面，在ITC相关化合物中，天然存在的4-[(4′-O-乙酰基-α-L-鼠李糖基氧)苄基]ITC以及市售的烯丙基-和苄基-ITC均显著抑制激活，表明异硫氰酸根基团是活性中的关键结构因素。
• Faizi, Shaheen; Siddiqui, Bina Shaheen; Saleem, Rubeena, Journal of the Chemical Society. Perkin transactions I, 1992, # 23, p. 3237 - 3242
  作者：Faizi, Shaheen、Siddiqui, Bina Shaheen、Saleem, Rubeena、Siddiqui, Salimuzzaman、Aftab, Khalid、Gilani, Anwar-ul-Hassan

  DOI：——

  日期：——
• Synthesis of active principles from the leaves of Moringa oleifera using S-pent-4-enyl thioglycosides
  作者：Michael Leuck、Horst Kunz

  DOI：10.1016/s0008-6215(98)00223-7

  日期：1998.11

  alpha-L-Rhamnosides of 4-hydroxy-benzyl compounds with nitrile, carbamate, and thiocarbamate groups occurring in Moringa oleifera leaf extracts and the alpha-L-rhamnoside of anisaldehyde derivatives were synthesised. Electrophilic activation of S-pent-4-enyl thiorhamnosides was applied for the construction of glycosidic linkages. (C) 1998 Elsevier Science Ltd. All rights reserved.