5-O-benzoyl-3-O-allyl-1,4-anhydro-D-ribitol | 478044-35-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-O-benzoyl-3-O-allyl-1,4-anhydro-D-ribitol
• 英文别名: [(2R,3S,4S)-4-hydroxy-3-prop-2-enoxyoxolan-2-yl]methyl benzoate
• CAS: 478044-35-8
• 化学式: C₁₅H₁₈O₅
• 分子量: 278.305
• InChiKey: OMTCFEGFCXTKQG-MJBXVCDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-O-benzoyl-3-O-allyl-1,4-anhydro-D-ribitol 在 吡啶 、 18-冠醚-6 、 四丁基氟化铵 、 potassium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 32.0h， 生成 8-bromo-N¹-(5''-O-benzoyl-1'',4''-anhydro-2''-deoxy-3''-O-allyl-D-ribitol-2''-yl)-2',3'-di-O-acetylinosine
  参考文献：
  名称：

  Syntheses and Calcium-Mobilizing Evaluations of N-Glycosyl-Substituted Stable Mimics of Cyclic ADP-Ribose

  摘要：

  Cyclic ADP-ribose (cADPR) is not only a potent endogenous calcium modulator but also a second messenger. However, studies on the mechanism of cADPR action were limited due to its instability and lack of available structural modifications in the N-1-glyosyl unit of cADPR. In the present work, a series of N-1-glycosyl mimics with different configurational glycosyls or an ether strand were designed and synthesized mimicking the furanose ring. S(N)2 substitutions were carried out between the protected inosine and glycosyl triflates to form the N-1-glycosylinosine derivatives, accompanied with some O-6-glyeosyl-substituted as side products. The intramolecular cyclization was followed the strategy described by Matsuda et al. It was found that the 8-unsubstituted substrate could also be used to construct the intramolecular cyclic pyrophosphate. The activities of NI-glycosyl-substituted cADPR mimics were evaluated by induced Ca2+ release in rat brain microsomes and HeLa cells. It was found that the configuration of the N-1-glycosyl moiety in cADPR is not a critical structural factor for retaining the activity of mobilizing Ca2+ release. More interestingly, the N-1-acyclic analogue 6 exhibited strong activity by inducing Ca2+ release in both rat brain microsomes and HeLa cells. It constitutes a useful tool for further studies.

  DOI：

  10.1021/jm010530l
• 作为产物：
  描述：

  3-O-Allyl-5-O-benzoyl-1,2-O-isopropylidene-α-D-ribofuranose 在 三乙基硅烷 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以83%的产率得到5-O-benzoyl-3-O-allyl-1,4-anhydro-D-ribitol
  参考文献：
  名称：

  Syntheses and Calcium-Mobilizing Evaluations of N-Glycosyl-Substituted Stable Mimics of Cyclic ADP-Ribose

  摘要：

  Cyclic ADP-ribose (cADPR) is not only a potent endogenous calcium modulator but also a second messenger. However, studies on the mechanism of cADPR action were limited due to its instability and lack of available structural modifications in the N-1-glyosyl unit of cADPR. In the present work, a series of N-1-glycosyl mimics with different configurational glycosyls or an ether strand were designed and synthesized mimicking the furanose ring. S(N)2 substitutions were carried out between the protected inosine and glycosyl triflates to form the N-1-glycosylinosine derivatives, accompanied with some O-6-glyeosyl-substituted as side products. The intramolecular cyclization was followed the strategy described by Matsuda et al. It was found that the 8-unsubstituted substrate could also be used to construct the intramolecular cyclic pyrophosphate. The activities of NI-glycosyl-substituted cADPR mimics were evaluated by induced Ca2+ release in rat brain microsomes and HeLa cells. It was found that the configuration of the N-1-glycosyl moiety in cADPR is not a critical structural factor for retaining the activity of mobilizing Ca2+ release. More interestingly, the N-1-acyclic analogue 6 exhibited strong activity by inducing Ca2+ release in both rat brain microsomes and HeLa cells. It constitutes a useful tool for further studies.

  DOI：

  10.1021/jm010530l

文献信息

• Syntheses and Calcium-Mobilizing Evaluations of <i>N</i>-Glycosyl-Substituted Stable Mimics of Cyclic ADP-Ribose
  作者：Li-Jun Huang、Yong-Yuan Zhao、Lan Yuan、Ji-Mei Min、Li-He Zhang

  DOI：10.1021/jm010530l

  日期：2002.11.1

  Cyclic ADP-ribose (cADPR) is not only a potent endogenous calcium modulator but also a second messenger. However, studies on the mechanism of cADPR action were limited due to its instability and lack of available structural modifications in the N-1-glyosyl unit of cADPR. In the present work, a series of N-1-glycosyl mimics with different configurational glycosyls or an ether strand were designed and synthesized mimicking the furanose ring. S(N)2 substitutions were carried out between the protected inosine and glycosyl triflates to form the N-1-glycosylinosine derivatives, accompanied with some O-6-glyeosyl-substituted as side products. The intramolecular cyclization was followed the strategy described by Matsuda et al. It was found that the 8-unsubstituted substrate could also be used to construct the intramolecular cyclic pyrophosphate. The activities of NI-glycosyl-substituted cADPR mimics were evaluated by induced Ca2+ release in rat brain microsomes and HeLa cells. It was found that the configuration of the N-1-glycosyl moiety in cADPR is not a critical structural factor for retaining the activity of mobilizing Ca2+ release. More interestingly, the N-1-acyclic analogue 6 exhibited strong activity by inducing Ca2+ release in both rat brain microsomes and HeLa cells. It constitutes a useful tool for further studies.