3-(溴甲基)-1,8-二甲氧基-9,10-蒽二酮 | 107960-84-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 3-(溴甲基)-1,8-二甲氧基-9,10-蒽二酮
• 英文名称: 3-(bromomethyl)-1,8-dimethoxy-9,10-anthracenedione
• 英文别名: 3-bromomethyl-1,8-dimethoxy-9,10-anthraquinone；3-(bromomethyl)-1,8-dimethoxyanthracene-9,10-dione
• CAS: 107960-84-9
• 化学式: C₁₇H₁₃BrO₄
• 分子量: 361.192
• InChiKey: BSOWZXFPBBGESB-UHFFFAOYSA-N

物化性质

• 熔点：
  176-178 °C
• 沸点：
  532.7±50.0 °C(Predicted)
• 密度：
  1.526±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(溴甲基)-1,8-二甲氧基-9,10-蒽二酮 在 氯化亚砜 、 氢溴酸 、 溶剂黄146 作用下， 以 乙醚 为溶剂， 生成 3-{[Bis-(2-chloro-ethyl)-amino]-methyl}-8-hydroxy-1-methoxy-anthraquinone
  参考文献：
  名称：

  潜在的新型抗癌药，衍生自香豆酚和大黄素。一些构效关系研究。

  摘要：

  DOI：

  10.1021/jm00397a002
• 作为产物：
  描述：

  大黄酚 在 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 、 potassium carbonate 作用下， 以 四氯化碳 、 丙酮 为溶剂， 反应 13.0h， 生成 3-(溴甲基)-1,8-二甲氧基-9,10-蒽二酮
  参考文献：
  名称：

  The influence of ion-pairing on the electroreductive cleavage of substituted 9,10-anthraquinones in DMF solution

  摘要：

  DOI：

  10.1021/jo00386a030

文献信息

• Intercalating agents with covalent bond forming capability. A novel type of potential anticancer agents. 2. Derivatives of chrysophanol and emodin
  作者：Masao Koyama、Kiyobumi Takahashi、Ting Chao Chou、Zbigniew Darzynkiewicz、Jan Kapuscinski、T. Ross Kelly、Kyoichi A. Watanabe

  DOI：10.1021/jm00127a032

  日期：1989.7

  Fifty-one new C-methyl-modified derivatives of the anthraquinones chrysophanol and emodin or their various methyl ethers were prepared for structure-activity relationship studies of anticancer activity against mouse leukemia L1210 and human leukemia HL-60 cells. Representative compounds were spectrophotometrically studied for their capacity to interact with natural and denatured DNA. In general, those

  制备了蒽醌chsophophanol和大黄素或它们的各种甲基醚的五十一种新的C-甲基修饰的衍生物，用于研究对小鼠白血病L1210和人白血病HL-60细胞的抗癌活性的结构-活性关系。用分光光度法研究了代表性化合物与天然和变性DNA相互作用的能力。通常，具有氨基功能的那些蒽醌与DNA相互作用。1,8-二甲氧基蒽醌不能嵌入DNA。但是，1-或8-单羟基单甲氧基蒽醌与DNA有一定程度的相互作用。分光光度法研究的化合物的DNA亲和力数据与细胞毒性作用之间没有明显的直接相关性。当在暴露的最初30分钟内抑制[3H] TdR掺入DNA中时，这些化合物在72小时内对细胞生长的抑制作用的细胞毒作用与它们的作用成反比。出人意料的是，一些显示出更高细胞毒性的化合物没有抑制初始TdR掺入（0-30分钟），而其他一些强烈抑制TdR掺入的化合物最初在72 h内没有细胞毒性。结果表明，这些化合物产生的细胞毒性是时间依赖性
• Derivatives of chryosphanol
  申请人：Sloan-Kettering Institute for Cancer Research

  公开号：US04966918A1

  公开（公告）日：1990-10-30

  The present invention concerns compounds of the formula: ##STR1## wherein R.sup.1 hydrogen, a hydroxyl group or a methoxy group; R.sup.2 is hydrogen or a methyl group; R.sup.3 is hydrogen or a methyl group; Y is a halogen, a secondary amino group or a tertiary amino group; and Z is hydrogen or a halogen. The invention further concerns pharmaceutical compositions which comprises the above-identified compound or the acid salts thereof, and the use of the compound or compositions for treating a malignancy in a subject.

  本发明涉及以下结构的化合物：##STR1## 其中 R.sup.1 是氢、羟基或甲氧基；R.sup.2 是氢或甲基；R.sup.3 是氢或甲基；Y 是卤素、二级氨基或三级氨基；Z 是氢或卤素。该发明还涉及包括上述化合物或其酸盐的药物组合物，以及将该化合物或组合物用于治疗受试者的恶性肿瘤。
• Derivatives of chrysophanol as topoisomerase II inhibitors
  申请人：Sloan-Kettering Institute For Cancer Research

  公开号：US05053431A1

  公开（公告）日：1991-10-01

  The present invention concerns compounds of the formula: ##STR1## wherein R.sup.1 is hydrogen, a hydroxy group or a methoxy group; R.sup.2 is hydrogen or a methyl group; R.sup.3 is hydrogen or a methyl group; Y is a secondary amino group (NHalkyl) or a tertiary amino group (N(alkyl).sub.2); and Z is hydrogen or a halogen. The invention further provides a method of inhibiting topoisomerase II using a compound having the structure: ##STR2## wherein R.sup.1 is hydrogen, a hydroxy group or a methoxy group; R.sup.2 is hydrogen or a methyl group; R.sup.3 is hydrogen or a methyl group; Y is a halogen, secondary amino group (NHalkyl) or a tertiary amino group (N(alkyl).sub.2); and Z is hydrogen or a halogen. The invention further concerns pharmaceutical compositions which comprise the above-identified compound or the acid salts thereof, and the use of the compound or compositions for treating a malignancy in a subject.

  本发明涉及以下结构的化合物：##STR1##其中R.sup.1为氢、羟基或甲氧基；R.sup.2为氢或甲基；R.sup.3为氢或甲基；Y为次级氨基（NHalkyl）或三级氨基（N(alkyl).sub.2）；Z为氢或卤素。该发明还提供了一种利用具有以下结构的化合物抑制拓扑异构酶II的方法：##STR2##其中R.sup.1为氢、羟基或甲氧基；R.sup.2为氢或甲基；R.sup.3为氢或甲基；Y为卤素、次级氨基（NHalkyl）或三级氨基（N(alkyl).sub.2）；Z为氢或卤素。该发明还涉及包含上述化合物或其酸盐的药物组合物，以及利用该化合物或组合物治疗受试者的恶性肿瘤的用途。
• Substituent effects upon the peak potentials and reductive cleavage rate constants of hydroxy- and methoxy-substituted 9,10-anthraquinones in 50% aqueous CH3CN: do they correlate?
  作者：Ronald L. Blankespoor、Elise L. Kosters、Alan J. Post、Derek P. Van Meurs

  DOI：10.1021/jo00004a049

  日期：1991.2

  A variety of hydroxy- and methoxy-substituted 2-(acetoxymethyl)-9,10-anthraquinones (2a-7a) were reduced electrochemically and with dithionite (S2O-4(2-)) in 50% aqueous CH3CN buffers over a wide pH range. Good to excellent yields of their corresponding reductive cleavage products, the substituted 2-methyl-9,10-anthraquinones 2b-7b, were obtained from most of these anthraquinone acetates, but only at higher pH. Rate constants for the reaction of 2-(acetoxymethyl)-9,10-anthraquinone (1a) with excess dithionite ranged from 1.0 x 10(-4) S-1 at pH values less than 7 to 4.0 x 10(-4) S-1 at a pH of 10, demonstrating that loss of acetate occurs in the rate-determining step and that cleavage occurs slower via the anthrahydroquinone of 1a than the conjugate base of the anthrahydroquinone. Substituent effects upon the reductive cleavage process were determined by measuring rate constants for those acetates that react cleanly with dithionite at pH 8. These effects, which are rationalized on the basis of resonance theory and intramolecular H bonding, correlate fairly well with the peak potentials (E(p)) of the reductive cleavage products of these acetates. Thus, electron-donating substituents on an anthraquinone acetate not only make it more difficult to reduce resulting in a more negative E(p) but also enhance the rate of acetate cleavage in the corresponding anthrahydroquinone.
• KOYAMA, MASAO;TAKAHASHI, KIYOBUMI;CHOU, TING-CHAO;DARZYNKIEWICZ, ZBIGNIEW+, J. MED. CHEM., 32,(1989) N, C. 1594-1599
  作者：KOYAMA, MASAO、TAKAHASHI, KIYOBUMI、CHOU, TING-CHAO、DARZYNKIEWICZ, ZBIGNIEW+

  DOI：——

  日期：——