phenyl 6-deoxy-6-(morpholin-4-yl)-β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 6-deoxy-6-(morpholin-4-yl)-β-D-glucopyranoside
• 英文别名: (2R,3S,4S,5R,6S)-2-(morpholin-4-ylmethyl)-6-phenoxyoxane-3,4,5-triol
• 化学式: C₁₆H₂₃NO₆
• 分子量: 325.362
• InChiKey: XOAAYZYEFSOVPL-IBEHDNSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  91.6
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 phenyl 6-deoxy-6-(morpholin-4-yl)-β-D-glucopyranoside 在 吡啶 作用下， 以56%的产率得到phenyl 2,3,4-tri-O-acetyl-6-deoxy-6-(morpholin-4-yl)-β-D-glucopyranoside
  参考文献：
  名称：

  Inhibition of some hepatic lysosomal glycosidases by ethanolamines and phenyl 6-deoxy-6-(morpholin-4-yl)-β-d-glucopyranoside

  摘要：

  The hepatic lysosomal glycosidases alpha-glucosidase and beta-glucuronidase were inhibited in vitro and in vivo by mono- and diethanolamines. The in vivo inhibition is dose dependent and occurs at a value less than LD50. Phenyl 6-deoxy-6-(morpholin-4-yl)-beta-D-glucopyranoside inhibited alpha-glucosidase both in vitro and in vivo. The treatment of the enzymes in vitro by ethanolamine exhibited a reversible inhibition of the mixed and competitive types for alpha-glucosidase and beta-glucuronidase, respectively. Diethanolamine showed a reversible inhibition of the competitive type for both enzymes. It is a potent inhibitor for beta-glucuronidase, in vitro, whose inhibition constant (K-i) is 5 x 10(-5) M. Phenyl 6-deoxy-6-(morpholin-4-yl)-beta-D-glucopyranoside is a potent inhibitor only for hepatic alpha-glucosidase with a K-i value of 1.6 x 10(-5) M. The pattern of the pH dependence of enzymic activity was not affected by ethanolamine inhibition. The magnitude of the inhibition of enzymes is dependent on the structure of the inhibitor. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00076-2
• 作为产物：
  描述：

  吗啉 、 苯基-BETA-葡萄糖吡喃糖苷 以 N,N-二甲基甲酰胺 为溶剂， 以44%的产率得到phenyl 6-deoxy-6-(morpholin-4-yl)-β-D-glucopyranoside
  参考文献：
  名称：

  Inhibition of some hepatic lysosomal glycosidases by ethanolamines and phenyl 6-deoxy-6-(morpholin-4-yl)-β-d-glucopyranoside

  摘要：

  The hepatic lysosomal glycosidases alpha-glucosidase and beta-glucuronidase were inhibited in vitro and in vivo by mono- and diethanolamines. The in vivo inhibition is dose dependent and occurs at a value less than LD50. Phenyl 6-deoxy-6-(morpholin-4-yl)-beta-D-glucopyranoside inhibited alpha-glucosidase both in vitro and in vivo. The treatment of the enzymes in vitro by ethanolamine exhibited a reversible inhibition of the mixed and competitive types for alpha-glucosidase and beta-glucuronidase, respectively. Diethanolamine showed a reversible inhibition of the competitive type for both enzymes. It is a potent inhibitor for beta-glucuronidase, in vitro, whose inhibition constant (K-i) is 5 x 10(-5) M. Phenyl 6-deoxy-6-(morpholin-4-yl)-beta-D-glucopyranoside is a potent inhibitor only for hepatic alpha-glucosidase with a K-i value of 1.6 x 10(-5) M. The pattern of the pH dependence of enzymic activity was not affected by ethanolamine inhibition. The magnitude of the inhibition of enzymes is dependent on the structure of the inhibitor. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00076-2

文献信息

• COMPOSITIONS FOR CANCER TREATMENT
  申请人：Engene, Inc.

  公开号：EP1556088A2

  公开（公告）日：2005-07-27
• Cancer treatment by metabolic modulations
  申请人：Pownall Scott

  公开号：US20050202559A1

  公开（公告）日：2005-09-15

  The invention provides compositions and methods for inhibiting the growth or proliferation of hyperproliferative cells or inducing regression of hyperproliferative cells. More specifically, the invention provides compositions and methods for stimulating glycogen accumulation in target cells (e.g., hyperproliferative cells) in order to increase glycogen to a level that is toxic to the target cell.
• CANCER TREATMENT BY METABOLIC MODULATIONS
  申请人：POWNALL SCOTT

  公开号：US20090041740A1

  公开（公告）日：2009-02-12

  The invention provides compositions and methods for inhibiting the growth or proliferation of hyperproliferative cells or inducing regression of hyperproliferative cells. More specifically, the invention provides compositions and methods for stimulating glycogen accumulation in target cells (e.g., hyperproliferative cells) in order to increase glycogen to a level that is toxic to the target cell.
• [EN] CANCER TREATMENT BY METABOLIC MODULATIONS<br/>[FR] TRAITEMENT DE CANCER PAR DES MODULATIONS METABOLIQUES
  申请人：ENGENE INC

  公开号：WO2004039412A2

  公开（公告）日：2004-05-13

  The invention provides compositions and methods for inhibiting the growth or proliferation of hyperproliferative cells or inducing regression of hyperproliferative cells. More specifically, the invention provides compositions and methods for stimulating glycogen accumulation in target cells (e.g., hyperproliferative cells) in order to increase glycogen to a level that is toxic to the target cell.
• Inhibition of some hepatic lysosomal glycosidases by ethanolamines and phenyl 6-deoxy-6-(morpholin-4-yl)-β-d-glucopyranoside
  作者：Mahmoud Balbaa、Neama Abdel-Hady、Fatma El-Rashidy、Laila Awad、El-Sayed H. El-Ashry、Richard R. Schmidt

  DOI：10.1016/s0008-6215(99)00076-2

  日期：1999.4

  The hepatic lysosomal glycosidases alpha-glucosidase and beta-glucuronidase were inhibited in vitro and in vivo by mono- and diethanolamines. The in vivo inhibition is dose dependent and occurs at a value less than LD50. Phenyl 6-deoxy-6-(morpholin-4-yl)-beta-D-glucopyranoside inhibited alpha-glucosidase both in vitro and in vivo. The treatment of the enzymes in vitro by ethanolamine exhibited a reversible inhibition of the mixed and competitive types for alpha-glucosidase and beta-glucuronidase, respectively. Diethanolamine showed a reversible inhibition of the competitive type for both enzymes. It is a potent inhibitor for beta-glucuronidase, in vitro, whose inhibition constant (K-i) is 5 x 10(-5) M. Phenyl 6-deoxy-6-(morpholin-4-yl)-beta-D-glucopyranoside is a potent inhibitor only for hepatic alpha-glucosidase with a K-i value of 1.6 x 10(-5) M. The pattern of the pH dependence of enzymic activity was not affected by ethanolamine inhibition. The magnitude of the inhibition of enzymes is dependent on the structure of the inhibitor. (C) 1999 Elsevier Science Ltd. All rights reserved.