N-(2'-piperazinylethyl)benzo[k, l]thioxanthene-3,4-dicarboximide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: N-(2'-piperazinylethyl)benzo[k, l]thioxanthene-3,4-dicarboximide
• 英文别名: N-(2'-piperazinylethyl)benzo[k,l]thioxanthene-3,4-dicarboximide；14-(2-Piperazin-1-ylethyl)-8-thia-14-azapentacyclo[10.6.2.02,7.09,19.016,20]icosa-1(19),2,4,6,9,11,16(20),17-octaene-13,15-dione
• 化学式: C₂₄H₂₁N₃O₂S
• 分子量: 415.516
• InChiKey: MGXZMKQOIKNXMQ-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：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  78
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-溴-1,8-萘二甲酸酐 在 盐酸 、 potassium carbonate 、 溶剂黄146 、 sodium nitrite 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.33h， 生成 N-(2'-piperazinylethyl)benzo[k, l]thioxanthene-3,4-dicarboximide
  参考文献：
  名称：

  Thio-heterocylic naphthalimides with aminoalkyl side chains: novel alternative tools for photodegradation of genomic DNA without impairment on bioactivities of proteins

  摘要：

  Thio-heterocylic naphthalimides (R1-R5) were designed, synthesized and evaluated as nonmetallic and long-wavelength photocleavers. Some of them showed highly efficient abilities in the degradation of plasmid and genomic DNA under the mild conditions without obvious impairment on the proteins' bioactivities, when compared with frequently applied nucleic acids removal reagents or precipitants. Their differences in photodegradation selectivity to DNA rather than proteins were dependent on their photodamage mechanisms and binding modes with bio-macromolecules. When maize genomic DNA was used as substrate, 2.38 x 10(-4) M of R5 exhibited the nuclease activity of 8 Unit DNase 1, R5 has some characteristic as a typical catalyst as no consumption after two cycles of the photodegradation for DNA. The experiments of enzymatic activity assay and immunology activity analysis showed that R5 was safe to proteins, suggesting its potential in the removal of transgenic material during the preparation of bioactive proteins or enzyme preparations. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.12.012

文献信息

• Highly-efficient DNA photocleavers with long wavelength absorptions: thio-heterocyclic fused naphthalimides containing aminoalkyl side chains
  作者：Xuhong Qian、Yonggang Li、Yufang Xu、Yan Liu、Baoyuan Qu

  DOI：10.1016/j.bmcl.2004.02.059

  日期：2004.5

  Thio-heterocyclic fused naphthalimides with aminoalkyl side chains were designed, synthesized and evaluated. These compounds have long wavelength absorptions and binding affinities to Calf thymus DNA. They could photodamage supercoiled pBR322 DNA from form I (closed) to II (nicked) at a concentration as low as 0.5 muM and to form III (linear) at a concentration of 50 muM. A possible mechanism of superoxide anion was provided. (C) 2004 Elsevier Ltd. All rights reserved.
• SULFUR-CONTAINING NAPHTHALIMIDE DERIVATIVES
  申请人：Qian Xuhong

  公开号：US20080234287A1

  公开（公告）日：2008-09-25

  The invention discloses novel sulfur-containing naphthalimide derivatives, and the preparation and uses thereof. The conjugated plane of naphthalimide derivatives of the invention is enlarged by incorporating 5- or 6-membered heteroaromatic ring and/or introducing S heteroatom, thus increasing the anti-tumor activity of naphthalimide. The compounds of the invention displays significant inhibiting activities to the proliferation of various tumor cells such as human lung cancer, gastric cancer, liver cancer, leucocythemia and the like. The inhibition of cell proliferation is dose-dependent.
• COMPOSITIONS AND METHODS TO IMPROVE THE THERAPEUTIC BENEFIT OF SUBOPTIMALLY ADMINISTERED CHEMICAL COMPOUNDS INCLUDING SUBSTITUTED NAPHTHALIMIDES SUCH AS AMONAFIDE FOR THE TREATMENT OF IMMUNOLOGICAL, METABOLIC, INFECTIOUS, AND BENIGN OR NEOPLASTIC HYPERPROLIFERATIVE DISEASE CONDITIONS
  申请人：BROWN Dennis M.

  公开号：US20160067241A1

  公开（公告）日：2016-03-10

  The present invention describes methods and compositions for improving the therapeutic efficacy of therapeutic agents previously limited by suboptimal therapeutic performance by either improving efficacy as monotherapy or reducing side effects. Such methods and compositions are particularly applicable to naphthalimides such as amonafide or analogs, derivatives, or prodrugs thereof.
• US7541463B2
  申请人：——

  公开号：US7541463B2

  公开（公告）日：2009-06-02
• [EN] COMPOSITIONS AND METHODS TO IMPROVE THE THERAPEUTIC BENEFIT OF SUBOPTIMALLY ADMINISTERED CHEMICAL COMPOUNDS INCLUDING SUBSTITUTED NAPHTHALIMIDES SUCH AS AMONAFIDE FOR THE TREATMENT OF IMMUNOLOGICAL, METABOLIC, INFECTIOUS, AND BENIGN OR NEOPLASTIC HYPERPROLIFERATIVE DISEASE CONDITIONS<br/>[FR] COMPOSITIONS ET PROCÉDÉS PERMETTANT D'AMÉLIORER LE BÉNÉFICE THÉRAPEUTIQUE DES COMPOSÉS CHIMIQUES ADMINISTRÉS DE MANIÈRE SUBOPTIMALE COMPRENANT DES NAPHTALIMIDES SUBSTITUÉS TELS QUE L'AMONAFIDE POUR LE TRAITEMENT DES MALADIES IMMUNOLOGIQUES, MÉTABOLIQUES, INFECTIEUSES ET INFECTIEUSES OU HYPERPROLIFÉRATIVES ET NÉOPLASTIQUES.
  申请人：BROWN DENNIS M

  公开号：WO2014179528A2

  公开（公告）日：2014-11-06

  The present invention describes methods and compositions for improving the therapeutic efficacy of therapeutic agents previously limited by suboptimal therapeutic performance by either improving efficacy as monotherapy or reducing side effects. Such methods and compositions are particularly applicable to naphthalimides such as amonafide or analogs, derivatives, or prodrugs thereof.