5,6-dihydro-5,6-dioxo-3-nitro-naphtho[1',2':4,5]-imidazo[1,2-a]pyridine | 109497-35-0

• 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-3-nitro-naphtho[1',2':4,5]-imidazo[1,2-a]pyridine
• 英文别名: 3-nitro-naphtho[1',2':4,5]imidazo[1,2-a]pyridine-5,6-dione；3-nitro-naphth[1',2':4,5]imidazo[1,2-a]pyridine-5,6-dione；3-Nitro-naphth[1',2':4,5]imidazo[1,2-a]pyridin-5,6-dion；3-Nitronaphtho[1',2':4,5]imidazo[1,2-a]pyridine-5,6-dione；5-nitro-11,17-diazatetracyclo[8.7.0.02,7.011,16]heptadeca-1(10),2(7),3,5,12,14,16-heptaene-8,9-dione
• CAS: 109497-35-0
• 化学式: C₁₅H₇N₃O₄
• 分子量: 293.238
• InChiKey: SIQNPNRHNKQHFN-UHFFFAOYSA-N

物化性质

• 密度：
  1.67±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 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：
  97.3
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2933990090

反应信息

• 作为产物：
  描述：

  N-(3-氯-1,4-二氢-1,4-二氧代-2-萘基)乙酰胺 在 硫酸 、 硝酸 、 正丁醇 作用下， 生成 5,6-dihydro-5,6-dioxo-3-nitro-naphtho[1',2':4,5]-imidazo[1,2-a]pyridine
  参考文献：
  名称：

  Reactions of 2,3-Dichloro-1,4-naphthoquinone with 2-Aminopyridine and Related Amines¹

  摘要：

  DOI：

  10.1021/jo01085a026

文献信息

• 10.17179/excli2017-273
  作者：Pečiukaitytė-Alksnė, Milda、Šarlauskas, Jonas、Misevičienė, Lina、Marozienė, Audronė、Čėnas, Narimantas、Krikštopaitis, Kastis、Staniulytė, Zita、Anusevičius, Žilvinas

  DOI：10.17179/excli2017-273

  日期：——

  Nitrogen-based tetracyclic ortho-quinones (naphtho[1'2':4.5]imidazo[1,2-a]pyridine-5,6-diones, NPDOs) and their nitro-substituted derivatives (nitro-(P)NPDOs) were obtained by condensation of substituted 2,3-dichloro-1,4-naphthoquinones with 2-amino-pyridine and -pyrimidine and nitration at an elevated temperature. The structural features of the compounds as well as their global and regional electrophilic

  氮基四环邻醌（萘并[1'2'：4.5]咪唑并[1,2-a]吡啶-5,6-二酮，NPDOs）及其硝基取代衍生物（nitro-（P）NPDOs）是通过将取代的2，3-二氯-1，4-萘醌与2-氨基吡啶和-嘧啶缩合并在高温下硝化而获得。通过DFT计算来表征化合物的结构特征以及它们的整体和区域亲电力。这些化合物是单电子和双电子（氢化物）的高反应性底物，分别转移了P-450R（CPR; EC 1.6.2.4）和NQO-1（DTD; EC 1.6.99.2），同时产生了活性氧。根据P-450R和NQO-1介导的反应中的表观二阶速率常数（kcat / KM（Q））值定义的催化效率在3-6×107 M-1 s-范围内变化1和1.6-7.4×108 M-1 s-1。该化合物对肿瘤细胞系的细胞毒活性遵循浓度依赖性方式，对乳腺癌MCF-7具有相对较高的细胞毒性，CL50值为0.08-2.02 µM L-1，对肺癌A-549的毒性较低（CL50
• 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.
• US5981544A
  申请人：——

  公开号：US5981544A

  公开（公告）日：1999-11-09
• Reactions of 2,3-Dichloro-1,4-naphthoquinone with 2-Aminopyridine and Related Amines¹
  作者：WILLIAM L. MOSBY、RICHARD J. BOYLE

  DOI：10.1021/jo01085a026

  日期：1959.3