1,4-bis<<2-(diethylamino)ethyl>amino>anthracene-9,10-dione | 70477-04-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1,4-bis<<2-(diethylamino)ethyl>amino>anthracene-9,10-dione
• 英文别名: 1.4-Bis-(β-N-diethylamino-ethylamino)-anthrachinon；1,4-bis{[2-(diethylamino)ethyl]amino}anthracene-9,10-dione；9,10-Anthracenedione, 1,4-bis((2-(diethylamino)ethyl)amino)-；1,4-bis[2-(diethylamino)ethylamino]anthracene-9,10-dione
• CAS: 70477-04-2
• 化学式: C₂₆H₃₆N₄O₂
• 分子量: 436.597
• InChiKey: SKFYKJLSKFOQLM-UHFFFAOYSA-N

物化性质

• 熔点：
  109 °C
• 沸点：
  618.2±55.0 °C(Predicted)
• 密度：
  1.156±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  64.7
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 海关编码：
  2922399090

反应信息

• 作为产物：
  描述：

  1,4-双[(2-羟乙基)氨基]蒽醌 在 吡啶 作用下， 以 甲醇 、 苯 为溶剂， 反应 11.0h， 生成 1,4-bis<<2-(diethylamino)ethyl>amino>anthracene-9,10-dione
  参考文献：
  名称：

  Dzieduszycka; Stefanska; Kolodziejczyk, Farmaco, Edizione Scientifica, 1987, vol. 42, # 3, p. 219 - 226

  摘要：

  DOI：

文献信息

• [EN] ANTI-CANCER COMPOUNDS
  申请人：NATIONAL RESEARCH DEVELOPMENT CORPORATION

  公开号：WO1991005824A1

  公开（公告）日：1991-05-02

  (EN) Compounds of formula (I) in which R1, R2, R3 and R4 are each separately selected from hydrogen, X, NH-A-NHR and NH-A-N(O)R'R'' wherein X is hydroxy, halogeno, amino, C1-4 alkoxy or C2-8 alkanoyloxy, A is a C2-4 alkylene group with a chain length between NH and NHR or N(O)R'R'' of a least 2 carbon atoms and R, R' and R'' are each separately selected from C1-4 alkyl groups and C2-4 hydroxyalkyl and C2-4 dihydroxyalkyl groups in which the carbom atom attached to the nitrogen atom does not carry a hydroxy group and no carbon atom is substituted by two hydroxy groups, or R' and R'' together are a C2-6 alkylene group which with the nitrogen atom to which R' and R'' are attached forms a heterocyclic group having 3 to 7 atoms in the ring, but with the proviso that at least one of R1 to R4 is a group NH-A-N(O)R'R'', and physiologically acceptable salts thereof are of value in the treatment of cancer.(FR) Composés de formule (I) où R1, R2, R3 et R4 sont chacun sélectionnés séparément à partir de l'hydrogène, X, NH-A-NHR et NH-A-A(O)R'R'' où X est hydroxy, halogéno, amino, C1-4 alkoxy ou C2-8 alkanoyloxy, A est un groupe alkylène C2-4 à longueur de chaîne entre NH et NHR ou N(O)R'R'' d'au moins deux atomes de carbone et R, R' et R'' sont chacun sélectionnés séparément à partir de groupes alkyle C1-4 et de groupes hydroxyalkyle C2-4 et dihydroxyalkyle C2-4 où l'atome de carbone attaché à l'atome d'azote ne porte pas de groupe hydroxy et aucun atome de carbone n'est substitué par deux groupes hydroxy, ou R' et R'' ensemble sont un groupe alkylène C2-6 qui, avec l'atome d'azote auquel R' et R'' sont attachés, forme un groupe hétérocyclique ayant de 3 à 7 atomes dans l'anneau mais sous condition qu'au moins l'un de R1 à R4 soit un groupe NH-A-N(O)R'R'' et que ses sels physiologiquement acceptables soient valables dans le traitement du cancer.

  化合物的化学式为（I），其中R1、R2、R3和R4分别独立地选择自氢、X、NH-A-NHR和NH-A-N（O）R'R''，其中X是羟基、卤素、氨基、C1-4烷氧基或C2-8烷酰氧基，A是C2-4烷基链，在NH和NHR或N（O）R'R''之间具有至少2个碳原子，R、R'和R''分别独立地选择自C1-4烷基和C2-4羟基烷基和C2-4二羟基烷基，其中连接氮原子的碳原子不带有羟基，且没有碳原子被两个羟基取代，或者R'和R''在一起是C2-6烷基链，与R'和R''附着的氮原子一起形成一个具有3到7个原子的杂环基团，但至少R1到R4中的一个是NH-A-N（O）R'R''的群，其生理上可接受的盐对于癌症的治疗具有价值。
• Method of treating tumors in warm-blooded animals
  申请人：American Cyanamid Company

  公开号：US04540583A1

  公开（公告）日：1985-09-10

  This disclosure describes novel compositions of matter useful as growth inhibitors of transplanted tumors in mammals and the method of inducing the regression and/or palliation of leukemia and solid tumors in mammals therewith, the active ingredients of said compositions of matter being certain symmetrical 1,4-bis(substituted-amino)anthraquinones and the non-toxic acid-addition salts thereof.

  本披露描述了一种新型物质组合，可用作哺乳动物移植肿瘤的生长抑制剂，并通过该方法诱导哺乳动物白血病和实体肿瘤的回归和/或缓解，所述物质组合的活性成分为某些对称的1,4-双（取代氨基）蒽醌及其非毒性酸盐。
• Anti-cancer compounds
  申请人：National Research Development Corporation

  公开号：US05132327A1

  公开（公告）日：1992-07-21

  Compounds of formula (I) ##STR1## in which R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are each separately selected from hydrogen, X, NH--A--NHR and NH--A--N(O)R'R" wherein X is hydroxy, halogeno, amino, C.sub.1-4 alkoxy or C.sub.2-8 alkanoyloxy, A is a C.sub.2-4 alkylene group with a chain length between NH and NHR or N(O)R'R" of at least 2 carbon atoms and R, R' and R" are each separately selected from C.sub.1-4 alkyl groups and C.sub.2-4 hydroxyalkyl and C.sub.2-4 dihydroxyalkyl groups in which the carbon atom attached to the nitrogen atom does not carry a hydroxy group and no carbon atom is substituted by two hydroxy groups, or R' and R" together are a C.sub.2-6 alkylene group which with the nitrogen atom to which R" and R" are attached forms a heterocyclic group having 3 to 7 atoms in the ring, but with the proviso that at least one of R.sub.1 to R.sub.4 is a group NH--A--N(O)R'R", and physiologically acceptable salts thereof are of value in the treatment of cancer.

  式(I)化合物的组成：其中R1、R2、R3和R4都分别从氢、X、NH-A-NHR和NH-A-N（O）R'R"中选择，其中X是羟基、卤素、氨基、C1-4烷氧基或C2-8烷酰氧基，A是具有链长在NH和NHR或N（O）R'R"之间的C2-4烷基链，R、R'和R"都分别从C1-4烷基和C2-4羟基烷基和C2-4双羟基烷基中选择，其中与氮原子连接的碳原子不带有羟基，且没有碳原子被两个羟基取代，或者R'和R"一起是一个C2-6烷基链，与R"和R"连接的氮原子形成具有3到7个原子的杂环基团，但必须至少有一个R1到R4是NH-A-N（O）R'R"基团。这些化合物的生理上可接受的盐在癌症治疗中具有价值。
• Deuterated compounds and uses thereof
  申请人：Biostatus Limited

  公开号：US10385009B2

  公开（公告）日：2019-08-20

  An anthraquinone compound of formula I (such as the compounds of formulae II to X) and processes for making the same are provided. Pharmaceutical compositions for use in the treatment of cancer, optionally in combination with an agent capable of reducing the level of oxygenation of a tumor, are also provided. Additionally, an option for combination with chemotherapeutic and radiotherapeutic modalities to enhance overall tumor cell kill is provided. Methods for the detection of cellular hypoxia, both in vivo and in vitro, are additionally provided.

  提供了式 I 的蒽醌化合物（如式 II 至 X 的化合物）及其制造工艺。还提供了用于治疗癌症的药物组合物，可选择与能够降低肿瘤氧合水平的制剂结合使用。此外，还提供了一种与化疗和放射治疗方式相结合的方案，以增强对肿瘤细胞的整体杀伤力。此外，还提供了体内和体外检测细胞缺氧的方法。
• Comparative computer graphics and solution studies of the DNA interaction of substituted anthraquinones based on doxorubicin and mitoxantrone
  作者：Suhail A. Islam、Stephen Neidle、Bijukumar M. Gandecha、Malcolm Partridge、Laurence H. Patterson、Jeffrey R. Brown

  DOI：10.1021/jm00145a003

  日期：1985.7

  1-[[(Diethylamino)ethyl]amino]- and 1,4-, 1,5-, and 1,8-bis[[(diethylamino)ethyl]amino]anthraquinones are shown to intercalate into DNA. Computer graphics modelling of their intercalation into the self-complementary deoxydinucleoside d(CpG) showed differences in binding properties. While the 1-substituted compound can bind from either groove, the 1,8-disubstituted compound binds with both substituents in the major groove. In the low-energy state of the complex with the 1,5-disubstituted compound, this ligand "straddles" the site with a substituent in each groove--to do this, the compound must bind to a non-base-paired region, so inducing base pairing. The 1,4-compound binds from the major groove; "straddling" is also possible if full minimization of deoxydinucleoside geometry is performed. The differences in binding mode and interaction energies are reflected in the affinities of interaction (1,5- greater than 1,4- much greater than 1,8- greater than 1-); also the antiproliferative effects in vitro are in general agreement with this ranking.