2-(1,2-dihydrobenzo[c,d]indol-2-yliden)malononitrile | 118739-11-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(1,2-dihydrobenzo[c,d]indol-2-yliden)malononitrile
• 英文别名: 2-(1,2-dihydrobenzo[cd]indol-2-yliden)malononitrile；2-(benzo[c,d]indol-2(1H)-ylidene)malononitrile；2-(1H-benzo[cd]indol-2-ylidene)propanedinitrile
• CAS: 118739-11-0
• 化学式: C₁₄H₇N₃
• 分子量: 217.23
• InChiKey: VSPPAHXSTYFAGO-UHFFFAOYSA-N

物化性质

• 熔点：
  >300 °C
• 沸点：
  414.2±45.0 °C(Predicted)
• 密度：
  1.361±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  59.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(1,2-dihydrobenzo[c,d]indol-2-yliden)malononitrile 在 甲醇 、 tin(II) chloride dihdyrate 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Design and synthesis of benzo[c,d]indolone-pyrrolobenzodiazepine conjugates as potential anticancer agents

  摘要：

  A series of benzo[c,d]indol-2(1H)one-PBD conjugates (11a-I) have been designed and synthesized as potential anticancer agents. These compounds were prepared by linking the C8-position of DC-81 with a benzo[c,d]indol-2(1H)one moiety through different alkane spacers in good yields and confirmed by H-1 NMR, mass and HRMS data. The DNA binding ability of these conjugates was evaluated by thermal denaturation studies and interestingly, compound 111 showed enhanced DNA binding ability. These compounds were also evaluated for their anticancer activity in selected human cancer cell lines of lung, skin, colon and prostate by using MTT assay method. These new conjugates showed promising anticancer activity with IC50 values ranging from 1.05 to 36.49 mu M. Moreover, cell cycle arrest in SubG1 phase was observed upon treatment of A549 cells with 1 and 2 mu M (IC50) concentrations of compound 111 and it induced apoptosis. This is confirmed by Annexin V-FITC, Hoechst staining, caspase-3 activity as well as DNA fragmentation analysis. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.12.003
• 作为产物：
  描述：

  N-羟基-1,8-萘二甲酰亚胺 在 对甲苯磺酰氯 、 三氯氧磷 作用下， 以 甲苯 为溶剂， 反应 5.0h， 生成 2-(1,2-dihydrobenzo[c,d]indol-2-yliden)malononitrile
  参考文献：
  名称：

  Design and synthesis of benzo[c,d]indolone-pyrrolobenzodiazepine conjugates as potential anticancer agents

  摘要：

  A series of benzo[c,d]indol-2(1H)one-PBD conjugates (11a-I) have been designed and synthesized as potential anticancer agents. These compounds were prepared by linking the C8-position of DC-81 with a benzo[c,d]indol-2(1H)one moiety through different alkane spacers in good yields and confirmed by H-1 NMR, mass and HRMS data. The DNA binding ability of these conjugates was evaluated by thermal denaturation studies and interestingly, compound 111 showed enhanced DNA binding ability. These compounds were also evaluated for their anticancer activity in selected human cancer cell lines of lung, skin, colon and prostate by using MTT assay method. These new conjugates showed promising anticancer activity with IC50 values ranging from 1.05 to 36.49 mu M. Moreover, cell cycle arrest in SubG1 phase was observed upon treatment of A549 cells with 1 and 2 mu M (IC50) concentrations of compound 111 and it induced apoptosis. This is confirmed by Annexin V-FITC, Hoechst staining, caspase-3 activity as well as DNA fragmentation analysis. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.12.003

文献信息

• 一类含苯并噻唑的苯并[c ,d]吲哚-2(1H)-酮 类衍生物，其制备方法及应用
  申请人：大连理工大学

  公开号：CN106432219B

  公开（公告）日：2019-04-05

  本发明公开一类含苯并噻唑的苯并[c,d]吲哚‑2(1H)‑酮类衍生物，其制备方法及应用，所述衍生物具有通式Y的结构，其中R为‑H或‑Br，n＝2、3或4。本发明通过在苯并[c,d]吲哚‑2(1H)‑酮母体上引入苯并噻唑基团，设计合成了一类含苯并噻唑的苯并[c,d]吲哚‑2(1H)‑酮衍生物。该类衍生物对乳腺癌和宫颈癌等多种不同组织来源的肿瘤细胞具有抑制生长的活性，而对人体正常细胞的抑制活性较小，在制备抑制肿瘤细胞生长药物中具有广阔的前景。
• 含三唑侧链苯并[c,d]吲哚-2(1H)-酮类化合物 及其应用
  申请人：大连理工大学

  公开号：CN104072485B

  公开（公告）日：2016-08-24

  本发明涉及一类含三唑侧链苯并[c,d]吲哚‑2(1H)‑酮类化合物及其应用。所述化合物具有以下的化学分子结构通式Y。本发明通过缩合、取代、叠氮化、“Click chemistry”等反应，在萘内酰亚胺的2位引入生物活性的丙二腈结构来维持其较好的抗肿瘤活性，并通过柔性侧链引入具有生物活性的三唑结构和各种环状胺来改善该系列衍生物的溶解性，同时提高药效、降低毒副作用，设计合成了一类具有广泛的抗肿瘤活性的化合物，该类化合物对宫颈癌、肝癌、乳腺癌等多种不同组织来源的肿瘤细胞的正常生长具有较好的抑制作用。
• Novel DNA intercalators without basic side chains as efficient antitumor agents: Design, synthesis and evaluation of benzo-[c,d]-indol-malononitrile derivatives
  作者：Xiaolian Li、Qianqian Wang、Yang Qing、Yanjie Lin、Yingli Zhang、Xuhong Qian、Jingnan Cui

  DOI：10.1016/j.bmc.2010.03.017

  日期：2010.5

  Several 2-(substituted benzo[c,d]indol-2(1H)-ylidene)malononitriles have been designed and synthesized. Their DNA binding, antitumor and DNA damaging properties were evaluated. All the compounds exhibited efficient antitumor activities with preference to be against the tumor cell line 7721 rather than the tumor cell line MCF-7. Compound 1f could intercalate into DNA entirely presumably by the good

  已经设计并合成了几种2-（取代的苯并[ c，d ]吲哚-2（1H）-亚烷基）丙二腈。评估了它们的DNA结合，抗肿瘤和DNA损伤特性。所有化合物均表现出有效的抗肿瘤活性，优选针对肿瘤细胞株7721而不是针对肿瘤细胞MCF-7。推测化合物1f可以完全插入到DNA中，这是由于羰基与苯并[ c，d ]吲哚部分的良好共轭。更重要的是，1F表现出对MCF-7细胞与IC有力毒性50 0.003μM和分别针对7721个细胞在0.115μM。
• Design and synthesis of benzo[c,d]indolone-pyrrolobenzodiazepine conjugates as potential anticancer agents
  作者：Ahmed Kamal、G. Ramakrishna、V. Lakshma Nayak、P. Raju、A.V. Subba Rao、A. Viswanath、M.V.P.S. Vishnuvardhan、Sistla Ramakrishna、G. Srinivas

  DOI：10.1016/j.bmc.2011.12.003

  日期：2012.1

  A series of benzo[c,d]indol-2(1H)one-PBD conjugates (11a-I) have been designed and synthesized as potential anticancer agents. These compounds were prepared by linking the C8-position of DC-81 with a benzo[c,d]indol-2(1H)one moiety through different alkane spacers in good yields and confirmed by H-1 NMR, mass and HRMS data. The DNA binding ability of these conjugates was evaluated by thermal denaturation studies and interestingly, compound 111 showed enhanced DNA binding ability. These compounds were also evaluated for their anticancer activity in selected human cancer cell lines of lung, skin, colon and prostate by using MTT assay method. These new conjugates showed promising anticancer activity with IC50 values ranging from 1.05 to 36.49 mu M. Moreover, cell cycle arrest in SubG1 phase was observed upon treatment of A549 cells with 1 and 2 mu M (IC50) concentrations of compound 111 and it induced apoptosis. This is confirmed by Annexin V-FITC, Hoechst staining, caspase-3 activity as well as DNA fragmentation analysis. (C) 2011 Elsevier Ltd. All rights reserved.