leuco-1,4,5,8-tetrahydroxyanthraquinone | 69837-14-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: leuco-1,4,5,8-tetrahydroxyanthraquinone
• 英文别名: 5,8-dihydroxyleucoquinizarin；9,10-Anthracenedione, 2,3-dihydro-1,4,5,8-tetrahydroxy-；5,8,9,10-tetrahydroxy-2,3-dihydroanthracene-1,4-dione
• CAS: 69837-14-5
• 化学式: C₁₄H₁₀O₆
• 分子量: 274.23
• InChiKey: QJQPINQAQJTYMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  115
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  leuco-1,4,5,8-tetrahydroxyanthraquinone 以 硝基苯 为溶剂， 生成 1,4,5,8-四羟基蒽醌
  参考文献：
  名称：

  Krasnosel'skaya, M. I.; Nikulina, N. L.; Tkachenko, S. S., Russian Journal of Applied Chemistry, 1987, vol. 60, # 10, p. 2151 - 2153

  摘要：

  DOI：
• 作为产物：
  描述：

  1,4,5,8-四羟基蒽醌 在 sodium dithionite 作用下， 生成 leuco-1,4,5,8-tetrahydroxyanthraquinone
  参考文献：
  名称：

  Heyer, Thomas; Niclas, Hans-Joachim; Dietzel, Stephan, Zeitschrift fur Chemie, 1989, vol. 29, # 4, p. 139 - 140

  摘要：

  DOI：

文献信息

• 1-(Aminoalkylamino)-5,8-dihydroxy-4-substituted-anthraquinones
  申请人：American Cyanamid Company

  公开号：US04428882A1

  公开（公告）日：1984-01-31

  This disclosure describes 1-(aminoalkylamino)-5,8-dihydroxy-4-substituted-anthraquinones useful as chelating agents and for inhibiting the growth of transplanted mouse tumors.

  本公开说明了1-(氨基烷基氨基)-5,8-二羟基-4-取代蒽醌，它们可用作螯合剂并抑制移植小鼠肿瘤的生长。
• Method of treating tumors in warm-blooded animals
  申请人：American Cyanamid Company

  公开号：US04418078A1

  公开（公告）日：1983-11-29

  This disclosure describes compositions of matter useful as inhibitors of transplanted mouse tumor growth, the active ingredient of said compositions of matter being 1,4-bis(3-aminopropylamino)-5,8-dihydroxyanthraquinone or the non-toxic acid-addition salts thereof.

  本公开说明了一种作为抑制移植小鼠肿瘤生长的物质组成，该物质组成的活性成分为1,4-双(3-氨丙基氨基)-5,8-二羟基蒽醌或其无毒酸盐。
• Use of alpha-di(lower alkoxy) anthraquinones in the synthesis of
  申请人：Toms River Chemical Corporation

  公开号：US03983145A1

  公开（公告）日：1976-09-28

  Alpha-dihydroxyanthraquinones used as intermediates in the synthesis of many dyestuffs, such as the Alizarin Saphirols (e.g. Color Constitution No. 63000, 63005, 63010, 63011, 63315 and 63610) can be replaced on an equimolar basis by alpha-di(lower alkoxy)anthraquinones. The alpha-di(lower alkoxy) anthraquinones can be converted in a single step, by treatment with oleum, to the corresponding alpha-dihydroxyanthraquinone-beta-disulfonic acids in almost quantitative yield. The corresponding diamine is obtained by dinitrating followed by reduction of the nitro groups. The known intermediate, leuco 1,4,5,8-tetrahydroxyanthraquinone (see C.I. No. 62500) can be obtained either by reduction of the diamine or by reduction of the dinitro compound. In one embodiment, the alpha-di(lower alkoxy)anthraquinone is obtained from dinitroanthraquinone by treatment thereof with methanol and KOH.

  α-二羟蒽醌是合成许多染料的中间体，如茜素蓝（例如，色素构成物号63000、63005、63010、63011、63315和63610），可以以α-二（低烷氧基）蒽醌的等摩尔基础进行替代。α-二（低烷氧基）蒽醌可以通过与油酸处理的单步转化，以几乎定量的产率得到相应的α-二羟蒽醌-β-二磺酸。通过二硝基化后还原硝基团，可以得到相应的二胺。已知的中间体，亚甲基蓝（见C.I. No. 62500）可以通过还原二胺或还原二硝基化合物得到。在一种实施例中，α-二（低烷氧基）蒽醌是通过用甲醇和KOH处理二硝基蒽醌得到的。
• 1,4-Bis(aminoalkylamino)-anthraquinones and leuco derivatives thereof
  申请人：American Cyanamid Company

  公开号：US04138415A1

  公开（公告）日：1979-02-06

  This disclosure describes 1,4-bis(substituted-amino)-5,6-dihydroxyanthraquinones and 1,4,5-tris(substituted-amino)-8-hydroxyanthraquinones useful as chelating agents, as curing catalysts for epoxy resins, and for inhibiting the growth of transplanted mouse tumors.

  本公开说明了1,4-双(取代氨基)-5,6-二羟基蒽醌和1,4,5-三(取代氨基)-8-羟基蒽醌，可用作螯合剂、环氧树脂的固化催化剂，并用于抑制移植小鼠肿瘤的生长。
• Antharquinone Compounds as Anti Cancer Compounds
  申请人：Patterson Laurence Hylton

  公开号：US20080027107A1

  公开（公告）日：2008-01-31

  Anthraquinone compounds of the general formula (I) or a salt thereof (Formula I) in which R 1 to R 4 are each selected from the group consisting of H, C 1-4 alkyl, X 1 , —NHR 0 N (Rs)2 in which R° is a C 1 l 12 alkanediyl and each R 5 is H or optionally substituted C 14 alkyl, and a group of formula (11) in which at least one of R 6 ,R 7 and R 8 is selected from X 2 , and X 2 substituted C 1-4 alkyl and any others are H or C 14 alkyl; R 9 is selected from H, C 1 4 alkyl, X 2 and X 2 substituted C 1-4 alkyl; m is 0 or 1; n is 1 or 2; X 1 is a halogen atom, a hydroxyl group, a C 1 . 6 alkoxyl group, an aryloxy group or an acyloxy group; and X 2 is a halogen atom, a hydroxyl group, a C 1 6 alkoxyl group, an aryloxy group or an acyloxy group; provided that at least one of R 1 to R 4 is a group of formula (II). The N-oxides are useful prodrugs which are selectively bioreduced in hypoxic tumours to the corresponding cyclic amine derivatives. The amine compounds are cytotoxic and may be used as alkylating agents having topoisomerase II inhibiting activities in cancer therapy.

  通式（I）或其盐（式I）的蒽醌化合物，其中R1至R4均选自H、C1-4烷基、X1、-NHR0N（Rs）2的群，其中R°是C1l12烷二基，每个R5是H或可选取代的C14烷基，以及式（II）的一组，其中至少有一个R6、R7和R8选自X2和X2取代的C1-4烷基，其余为H或C14烷基；R9选自H、C14烷基、X2和X2取代的C1-4烷基；m为0或1；n为1或2；X1为卤素原子、羟基、C1.6烷氧基、芳基氧基或酰氧基；X2为卤素原子、羟基、C16烷氧基、芳基氧基或酰氧基；前提是至少有一个R1至R4是式（II）的一组。N-氧化物是有用的前药，在低氧肿瘤中选择性地生物还原为相应的环状胺衍生物。胺化合物具有细胞毒性，并可用作具有拓扑异构酶II抑制活性的烷基化剂，用于癌症治疗。