3-(16,18-Dioxo-17-azapentacyclo[6.6.5.0(2,7).0(9,14).0(15,19)]nonadeca-2,4,6,9,11,13-hexaen-17-yl)benzoic acid | 313653-93-9

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基四氢萘木脂素
• 英文名称: 3-(16,18-Dioxo-17-azapentacyclo[6.6.5.0(2,7).0(9,14).0(15,19)]nonadeca-2,4,6,9,11,13-hexaen-17-yl)benzoic acid
• 英文别名: 3-(16,18-dioxo-17-azapentacyclo[6.6.5.02,7.09,14.015,19]nonadeca-2,4,6,9,11,13-hexaen-17-yl)benzoic acid
• CAS: 313653-93-9
• 化学式: C₂₅H₁₇NO₄
• mdl: MFCD00339837
• 分子量: 395.414
• InChiKey: FTUWSZLTOPTYLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  30
• 可旋转键数：
  2
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  74.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  dibenzobarallene 、 间氨基苯甲酸 以 N,N-二甲基甲酰胺 为溶剂， 以70%的产率得到3-(16,18-Dioxo-17-azapentacyclo[6.6.5.0(2,7).0(9,14).0(15,19)]nonadeca-2,4,6,9,11,13-hexaen-17-yl)benzoic acid
  参考文献：
  名称：

  Modular design of hosts involving a rigid succinimide framework and N-bonded lateral groups. Crystalline inclusion properties and crystal structures of inclusion compounds with dioxane, methanol, and DMF

  摘要：

  A series of crystalline host molecules comprising a characteristic 9,10-ethanoanthracene-11,12-dicarboxamide framework have been synthesized and studied with regard to their inclusion behavior. They follow a new design concept which is to convert a given molecule, presently of amine, aminophenol, amino alcohol, or amino acid type, by addition of a so-called "clathratogenic group" (inclusion promoting group) into a crystalline host. These hosts form crystalline inclusion compounds with a variety of uncharged organic molecules ranging from protic dipolar to rather apolar compounds (103 different inclusion species). Inclusion formation and binding modes depend on the structural features of the hosts, i.e., the type of functional groups, their number, and geometric factors. X-ray crystal structures of three inclusion species are reported: 1.dioxane (1:1) [P2(1)/n, a = 11.9757 (4) angstrom, b = 9.8442 (3) angstrom, c = 16.2371 (5) angstrom, beta = 109.196 (4)-degrees, Z = 4], 23.MeOH (1:1) [Pbca, a = 8.532 (1) angstrom, b = 18.865 (1) angstrom, c = 24.074 (2) angstrom, Z = 8], 24.DMF (1:1) [P2(1)/a, a = 15.217 (1) angstrom, b = 11.445 (1) angstrom, c = 26.685 (2) angstrom, beta = 106.15 (1)-degrees, Z = 8]. They show the compounds to be typical coordinatoclathrates with hydrogen bond interactions between host and guest. In the crystals of 1.dioxane (1:1), hydrophobically aggregated host molecules form rectangular cages, each with space enough for two H bonded guests. In 23.MeOH (1:1), the guest acts both as donor and acceptor in H bonds, resulting in endless H bonded chains of alternating host and guest molecules. The finite 1:1 host-guest associates in 24.DMF (1:1) are held together by characteristic O-H...O(C) and possibly als by (C)H...O-type interactions.

  DOI：

  10.1021/jo00026a018

文献信息

• [EN] ANTHRACENE BASED COMPOUNDS AND THEIR USES<br/>[FR] COMPOSÉS À BASE D'ANTHRACÈNE ET LEURS UTILISATIONS
  申请人：UNIV OF HERTFORDSHIRE HIGHER EDUCATION CORP

  公开号：WO2016181120A1

  公开（公告）日：2016-11-17

  The present invention relates to compounds of the general formula (A) and their applicability for use in the treatment or prophylaxis of a disease, in particular for use as in treatment of cancer, in particular for use as in treatment of pancreatic cancer, in particular as inhibitors of S100P/RAGE interaction in pancreatic cancer. In summary herein are presented a group of compounds for use as in treatment of cancer, in particular as inhibitors of S100P/RAGE interaction in pancreatic cancer. The compounds have general formula (A): (A) or may be a pharmaceutically acceptable salt, solvate, hydrate, polymorph, prodrug, codrug, cocrystal, tautomer, racemate, stereoisomer or mixture thereof. X is independently NO2 or H; and Y is independently H or a side group. The compounds all have a lower fused ring system based on nitroanthracene or anthracene. The group Y attached to the N of the succinimide group varies between the compounds. For example, Y may be substituted or non-substituted benzene ring. Alternatively, in some examples Y is a heteroaromatic system. It has been discovered from studies by the inventors that the compounds described will inhibit S100P/RAGE interaction and are therefore useful for treating pancreatic cancer.

  本发明涉及一般式（A）的化合物及其在治疗或预防疾病方面的适用性，特别是在癌症治疗中的应用，特别是在胰腺癌治疗中的应用，特别是作为胰腺癌中S100P/RAGE相互作用的抑制剂。总之，这里介绍了一组化合物，用于癌症治疗，特别是作为胰腺癌中S100P/RAGE相互作用的抑制剂。这些化合物具有一般式（A）：（A）或者可能是药用可接受的盐、溶剂化合物、水合物、多晶形、前药、共药、共晶、互变异构体、拉氏体异构体或其混合物。X独立地是NO2或H；Y独立地是H或侧基。所有这些化合物都基于硝基蒽或蒽的较低融合环系统。连接到琥酰亚胺基团的N的Y基团在这些化合物之间变化。例如，Y可能是取代或非取代的苯环。另外，在某些例子中，Y是一个杂环芳香系统。发明者的研究表明，所描述的化合物将抑制S100P/RAGE相互作用，因此对治疗胰腺癌是有用的。
• Modular design of hosts involving a rigid succinimide framework and N-bonded lateral groups. Crystalline inclusion properties and crystal structures of inclusion compounds with dioxane, methanol, and DMF
  作者：Edwin Weber、Stephan Finge、Ingeborg Csoeregh

  DOI：10.1021/jo00026a018

  日期：1991.12

  A series of crystalline host molecules comprising a characteristic 9,10-ethanoanthracene-11,12-dicarboxamide framework have been synthesized and studied with regard to their inclusion behavior. They follow a new design concept which is to convert a given molecule, presently of amine, aminophenol, amino alcohol, or amino acid type, by addition of a so-called "clathratogenic group" (inclusion promoting group) into a crystalline host. These hosts form crystalline inclusion compounds with a variety of uncharged organic molecules ranging from protic dipolar to rather apolar compounds (103 different inclusion species). Inclusion formation and binding modes depend on the structural features of the hosts, i.e., the type of functional groups, their number, and geometric factors. X-ray crystal structures of three inclusion species are reported: 1.dioxane (1:1) [P2(1)/n, a = 11.9757 (4) angstrom, b = 9.8442 (3) angstrom, c = 16.2371 (5) angstrom, beta = 109.196 (4)-degrees, Z = 4], 23.MeOH (1:1) [Pbca, a = 8.532 (1) angstrom, b = 18.865 (1) angstrom, c = 24.074 (2) angstrom, Z = 8], 24.DMF (1:1) [P2(1)/a, a = 15.217 (1) angstrom, b = 11.445 (1) angstrom, c = 26.685 (2) angstrom, beta = 106.15 (1)-degrees, Z = 8]. They show the compounds to be typical coordinatoclathrates with hydrogen bond interactions between host and guest. In the crystals of 1.dioxane (1:1), hydrophobically aggregated host molecules form rectangular cages, each with space enough for two H bonded guests. In 23.MeOH (1:1), the guest acts both as donor and acceptor in H bonds, resulting in endless H bonded chains of alternating host and guest molecules. The finite 1:1 host-guest associates in 24.DMF (1:1) are held together by characteristic O-H...O(C) and possibly als by (C)H...O-type interactions.