5,6-dihydro-5,6-dioxo-10-methyl-naphtho[1',2':4,5]-imidazo[1,2-a]pyridine | 192653-87-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5,6-dihydro-5,6-dioxo-10-methyl-naphtho[1',2':4,5]-imidazo[1,2-a]pyridine
• 英文别名: 14-Methyl-11,17-diazatetracyclo[8.7.0.02,7.011,16]heptadeca-1(10),2,4,6,12,14,16-heptaene-8,9-dione
• CAS: 192653-87-5
• 化学式: C₁₆H₁₀N₂O₂
• 分子量: 262.268
• InChiKey: CHUOMRAEJMQDOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  51.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氨基-4-甲基吡啶 、 2,3-二氯-1,4-萘醌 以 乙醇 为溶剂， 以61%的产率得到5,6-dihydro-5,6-dioxo-10-methyl-naphtho[1',2':4,5]-imidazo[1,2-a]pyridine
  参考文献：
  名称：

  Mono-- or diketone tetracyclic derivatives and therapeutical uses thereof

  摘要：

  有关四环类衍生物及其药用可接受盐的治疗用途的发明，其具有以下一般公式：##STR1## 其中，独立于其他：X为碳或氮原子，T为碳或氮原子，L为氧原子或酮官能团保护基团，R.sub.1为氢原子、卤素原子或C.sub.1至C.sub.5烷基基团，R.sub.2为氢原子、卤素原子、硝基基团或C.sub.1至C.sub.5烷基基团，n和m等于0或1，但不独立于其他，因此如果n等于1，则m等于0，如果n等于0，则m等于1。

  公开号：

  US05981544A1

文献信息

• Mono-- or diketone tetracyclic derivatives and therapeutical uses thereof
  申请人：Laboratoire Innothera

  公开号：US05981544A1

  公开（公告）日：1999-11-09

  Invention concerning the therapeutic use of tetracyclic derivatives and their pharmaceutically acceptable salts having the following general formula: ##STR1## in which, independently of the other: X is a carbon or nitrogen atom, T is a carbon or nitrogen atom, L is an oxygen atom or ketone functional protective group, R.sub.1 is an atom of hydrogen, an atom of halogen, or a C.sub.1 to C.sub.5 alkyl radical, R.sub.2 is a hydrogen atom, a halogen atom, a nitro radical, or a C.sub.1 to C.sub.5 alkyl radical, n and m are equal to 0 or to 1, but not independently of the other, so that if n is equal to 1, then m is equal to 0, and if n is equal to 0, then m is equal to 1.

  有关四环类衍生物及其药用可接受盐的治疗用途的发明，其具有以下一般公式：##STR1## 其中，独立于其他：X为碳或氮原子，T为碳或氮原子，L为氧原子或酮官能团保护基团，R.sub.1为氢原子、卤素原子或C.sub.1至C.sub.5烷基基团，R.sub.2为氢原子、卤素原子、硝基基团或C.sub.1至C.sub.5烷基基团，n和m等于0或1，但不独立于其他，因此如果n等于1，则m等于0，如果n等于0，则m等于1。
• US5981544A
  申请人：——

  公开号：US5981544A

  公开（公告）日：1999-11-09
• Naphtho[1′,2′:4,5]imidazo[1,2-a]pyridine-5,6-diones: Synthesis, enzymatic reduction and cytotoxic activity
  作者：Jonas Šarlauskas、Milda Pečiukaitytė-Alksnė、Lina Misevičienė、Audronė Marozienė、Evelina Polmickaitė、Zita Staniulytė、Narimantas Čėnas、Žilvinas Anusevičius

  DOI：10.1016/j.bmcl.2015.11.084

  日期：2016.1

  Naphtho[1',2':4,5]imidazo[1,2-a]pyridine-5,6-diones (NPDOs), a new type of N-heterocycle-fused o-quinones, have been synthesized. They have been found to be efficient electron-accepting substrates of NADPH-dependent single-electron-transferring P-450R and two-electron transferring NQO1, generating reactive oxygen species (ROS) with a concomitant decrease in NADPH, which is consistent with redox-cycling. The reactivity of NPDOs toward P-450R (in terms of k(cat)/K-m) varied in the range of 10(6)-10(7) M-1 s(-1), while their reduction by NQO1 proceeded much faster, approaching the diffusion control limit (k(cat)/K-m similar to 10(8)-10(9) M-1 s(-1)). NPDOs exhibited relatively high cytotoxic activity against human lung carcinoma (A-549) and breast tumor (MCF-7) cell lines (LC50 = 0.1-8.3 mu M), while promyelocytic leukemia cells (HL-60) were less sensitive to NPDOs (LC50 >= 10 mu M). 3-Nitro-substituted NPDO (11) revealed the highest potency against both A-549 and MCF-7 cell lines, with LC50 of 0.12 +/- 0.03 mu M and 0.28 +/- 0.08 mu M, respectively. Dicoumarol partly suppressed the activity of the compounds against A-594 and MCF-7 cell lines, suggesting that their cytotoxic action might be partially influenced by NQO1-mediated bioreductive activation. (C) 2015 Elsevier Ltd. All rights reserved.