(1S,3S)-3-羟基乙酰基-3,5,12-三羟基-10-甲氧基-6,11-二氧代-1,2,3,4,6,11-六氢-1-并四苯基3-(3-氰基-4-吗啉基)-2,3,6-三脱氧吡喃己糖苷 | 88254-07-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 蒽环类药物
• 中文名称: (1S,3S)-3-羟基乙酰基-3,5,12-三羟基-10-甲氧基-6,11-二氧代-1,2,3,4,6,11-六氢-1-并四苯基3-(3-氰基-4-吗啉基)-2,3,6-三脱氧吡喃己糖苷
• 英文名称: 3'-deamino-3'-(3-cyano-4-morpholinyl)doxorubicin
• 英文别名: cyanomorpholino-doxorubicin；3'-Deamino-3'-(3-cyanomorpholin-4-yl)doxorubicin；4-[(2S,3S,4S,6R)-3-hydroxy-2-methyl-6-[[(1S,3S)-3,5,12-trihydroxy-3-(2-hydroxyacetyl)-10-methoxy-6,11-dioxo-2,4-dihydro-1H-tetracen-1-yl]oxy]oxan-4-yl]morpholine-3-carbonitrile
• CAS: 88254-07-3
• 化学式: C₃₂H₃₄N₂O₁₂
• 分子量: 638.628
• InChiKey: YIMDLWDNDGKDTJ-QLKYHASDSA-N

物化性质

• 沸点：
  671.35°C (rough estimate)
• 密度：
  1.3397 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  46
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  216
• 氢给体数：
  5
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  (1S,3S)-3-羟基乙酰基-3,5,12-三羟基-10-甲氧基-6,11-二氧代-1,2,3,4,6,11-六氢-1-并四苯基3-(3-氰基-4-吗啉基)-2,3,6-三脱氧吡喃己糖苷 在 吡啶 、 氨 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 75.0h， 生成 14-O-(p-anisyldiphenylmethyl)-3'-deamino-3'-(3-cyano-4-morpholinyl)-5-iminodoxorubicin
  参考文献：
  名称：

  Intensely potent morpholinyl anthracyclines

  摘要：

  3'-Deamino-3'-(3-cyano-4-morpholinyl)doxorubicin is a new analogue that is 100 to 1000 times more potent than doxorubicin against tumors in cell culture or in mice, that is active by intraperitoneal, intravenous, or oral dosing, and that does not produce chronic myocardial lesions in mice. This analogue was encountered in studies on the reductive alkylation of doxorubicin and daunorubicin with 2,2' - oxybis [acetaldehyde], which constructs a morpholino ring incorporating the amino N. The morpholinyl nitrile byproducts are separated by virtue of their nonbasicity from the expected morpholino derivatives. The 13-dihydro and 5-imino derivatives are also described in this important new class of anthracyclines.

  DOI：

  10.1021/jm00371a014
• 作为产物：
  描述：

  2,2'-氧基二乙醛 、 盐酸多柔比星 在 sodium cyanoborohydride 作用下， 以 水 、 乙腈 为溶剂， 以30%的产率得到3'-deamino-3'-(4-morpholinyl)doxorubicin
  参考文献：
  名称：

  Intensely potent morpholinyl anthracyclines

  摘要：

  3'-Deamino-3'-(3-cyano-4-morpholinyl)doxorubicin is a new analogue that is 100 to 1000 times more potent than doxorubicin against tumors in cell culture or in mice, that is active by intraperitoneal, intravenous, or oral dosing, and that does not produce chronic myocardial lesions in mice. This analogue was encountered in studies on the reductive alkylation of doxorubicin and daunorubicin with 2,2' - oxybis [acetaldehyde], which constructs a morpholino ring incorporating the amino N. The morpholinyl nitrile byproducts are separated by virtue of their nonbasicity from the expected morpholino derivatives. The 13-dihydro and 5-imino derivatives are also described in this important new class of anthracyclines.

  DOI：

  10.1021/jm00371a014

文献信息

• Inhibiting denaturation of nucleic acid duplexes
  申请人：——

  公开号：US20030157520A1

  公开（公告）日：2003-08-21

  A solution for treating a nucleic acid duplex having a pH of from 3 to 11, comprising a soluble protein or mixture of proteins; and 0.1 mM to 10 mM divalent cations; wherein the nature and concentration of the protein or mixture of proteins is selected so that the solution is capable of inhibiting heat denaturation of a nucleic acid duplex.

  一种用于处理核酸双链体的溶液，其 pH 值为 3 至 11，包含可溶性蛋白质或蛋白质混合物；以及 0.1 mM 至 10 mM 的二价阳离子；其中蛋白质或蛋白质混合物的性质和浓度经过选择，以使溶液能够抑制核酸双链体的热变性。
• WALKER, MOSHER CAROL;LOW, TONG GEORGE;MC, INTOSH ACTON EDWARD
  作者：WALKER, MOSHER CAROL、LOW, TONG GEORGE、MC, INTOSH ACTON EDWARD

  DOI：——

  日期：——
• Zytostatisch wirksame Anthracyclinderivate
  申请人：BEHRINGWERKE Aktiengesellschaft

  公开号：EP0270992B1

  公开（公告）日：1994-06-08
• INHIBITING DENATURATION OF NUCLEIC ACID DUPLEXES
  申请人：Whatman Bioscience Limited

  公开号：EP1290003A1

  公开（公告）日：2003-03-12
• CODED MOLECULES FOR DETECTING TARGET ANALYTES
  申请人：Applera Corporation

  公开号：EP1954838A2

  公开（公告）日：2008-08-13