5-oxa-10-thia-8,9-diazacyclopenta[a]phenalene-4,6-dione | 625836-86-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-oxa-10-thia-8,9-diazacyclopenta[a]phenalene-4,6-dione
• 英文别名: 1,2,3-thiadiazol-1,8-naphthalic anhydride；3-Oxa-11-thia-12,13-diazatetracyclo[7.6.1.05,16.010,14]hexadeca-1(15),5,7,9(16),10(14),12-hexaene-2,4-dione
• CAS: 625836-86-4
• 化学式: C₁₂H₄N₂O₃S
• 分子量: 256.241
• InChiKey: RSZXHJKDRRGYCM-UHFFFAOYSA-N

物化性质

• 熔点：
  162-167 °C
• 沸点：
  522.3±42.0 °C(Predicted)
• 密度：
  1.746±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-oxa-10-thia-8,9-diazacyclopenta[a]phenalene-4,6-dione 在 N,N-二甲基乙二胺 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以70%的产率得到5-(N',N'-dimethylaminoethyl)-4H,6H-benzo[de]-1,2,3,-thiadiazol[5,4-g]isoquinoline-4,6-diketone
  参考文献：
  名称：

  SULFUR-CONTAINING NAPHTHOYLIMIDE DERIVATIVES

  摘要：

  公开号：

  EP1626050B1
• 作为产物：
  描述：

  4-mercapto-3-amino-1,8-naphthalic anhydride 在 盐酸 、 sodium nitrite 作用下， 反应 3.5h， 以86%的产率得到5-oxa-10-thia-8,9-diazacyclopenta[a]phenalene-4,6-dione
  参考文献：
  名称：

  Thiadiazole: A new family of intercalative photonuclease with electron transfer and radical mechanisms

  摘要：

  A new family of photonuclease, thiadiazole-naphthalimide were synthesized and evaluated. Thiadiazole group was incorporated for the first time. These compounds intercalated into DNA efficiently and damaged DNA as low as 10 muM photochemically. Mechanism experiment showed that electron transfer and radicals were involved. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00737-6

文献信息

• Thio-heterocylic naphthalimides with aminoalkyl side chains: novel alternative tools for photodegradation of genomic DNA without impairment on bioactivities of proteins
  作者：Qing Yang、Xuhong Qian、Jianqiang Xu、Yuanshe Sun、Yonggang Li

  DOI：10.1016/j.bmc.2004.12.012

  日期：2005.3.1

  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.
• Synthesis of thiazo- or thiadiazo- naphthalene carboxamides via mercuric intermediates and their antitumor and DNA photocleavage activities
  作者：Zhigang Li、Qing Yang、Xuhong Qian

  DOI：10.1016/j.tet.2005.03.135

  日期：2005.7

  Two kinds of thiazo- or thiadiazo- naphthalene carboxamides with aminoalkyl side chains at 5- or 6-position modified from naphthalimides were designed, synthesized and quantitatively evaluated as antitumor and DNA photocleaving agents. The compound with aminoalkyl side chain at 6-position showed stronger antitumor (A549, P388) and DNA photocleaving abilities than its isomer with that at 5-position. B-2, the most efficient DNA photocleaver, also exhibited the highest cytotoxicity with the IC50 of 2.53 and 0.11 mu M against cell lines of A549 and P388, respectively. These compounds also photocleaved DNA more efficiently than their corresponding naphthalimides. (c) 2005 Elsevier Ltd. All rights reserved.