5-chloro-3-[2-(4-chlorophenyl)-2-oxoethyl]-3-hydroxyindolin-2-one | 442573-47-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-chloro-3-[2-(4-chlorophenyl)-2-oxoethyl]-3-hydroxyindolin-2-one
• 英文别名: 5-chloro-3-[2-(4-chlorophenyl)-2-oxoethyl]-3-hydroxy-1,3-dihydro-2H-indol-2-one；5-chloro-3-[2-(4-chlorophenyl)-2-oxoethyl]-3-hydroxy-1H-indol-2-one
• CAS: 442573-47-9
• 化学式: C₁₆H₁₁Cl₂NO₃
• 分子量: 336.174
• InChiKey: VBPHTRWNFHXSCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-chloro-3-[2-(4-chlorophenyl)-2-oxoethyl]-3-hydroxyindolin-2-one 在 盐酸 作用下， 以 水 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Synthesis and biological evaluation of spiro[cyclopropane-1,3′-indolin]-2′-ones as potential anticancer agents

  摘要：

  Libraries of spiro[cyclopropane-1,3'-indolin]-2'-ones were synthesized and evaluated for their biological activity against five different human cancer cell lines HT-29 (colon cancer), DU-145 (prostate cancer), Hela (cervical cancer), A-549 (Lung cancer), and MCF-7 (breast cancer). Many compounds of the series exhibited promising anticancer activity (IC50 < 20 mu M) against the studied cell lines. Based on the screening results, a structure activity relationship (SAR) of the pharmacophore was proposed. Among the series compound 6b and 6u showed significant activity against human prostate cancer cell line, DU-145. Flow cytometric analysis showed that these two compounds arrested the cell cycle in the G0/G1 phase leading to caspase-3 dependent apoptotic cell death. Further, measurement of mitochondrial membrane potential and Annexin V-FITC assay also suggested that 6b and 6u induced cell death by apoptosis. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.08.056
• 作为产物：
  描述：

  5-氯靛红 、 对氯苯乙酮 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 0.08h， 生成 5-chloro-3-[2-(4-chlorophenyl)-2-oxoethyl]-3-hydroxyindolin-2-one
  参考文献：
  名称：

  通过三组分顺序串联反应合成新型的oxindolylpyrrolo [2,3- d ]嘧啶

  摘要：

  通过程序设定的pH值变化，可以合成5-（2-氧代吲哚-3-基）-1 H-吡咯并完成6-氨基尿嘧啶，靛红和乙酰苯的新型一锅三组分反应[2， 3 - d ]嘧啶-2,4（3 H，7 H）-二酮衍生物。以顺序串联方式进行反应，以良好至极好的收率得到羟吲哚取代的吡咯并[2，3- d ]嘧啶产物。尽管有时间安排，但所有过程都在一个锅中进行。这些新型化合物中的大多数在体外均显示出窄至良好的抗菌活性谱。

  DOI：

  10.1016/j.tet.2012.09.045

文献信息

• Chalcone based azacarboline analogues as novel antitubulin agents: Design, synthesis, biological evaluation and molecular modelling studies
  作者：Sahil Sharma、Charanjit Kaur、Abhishek Budhiraja、Kunal Nepali、Manish K. Gupta、A.K. Saxena、P.M.S. Bedi

  DOI：10.1016/j.ejmech.2014.08.005

  日期：2014.10

  The present study involves the design of a series of 3-aryl-9-acetyl-pyridazino[3,4-b]indoles as constrained chalcone analogues. A retrosynthetic route was proposed for the synthesis of target compounds. All the synthesized compounds were evaluated for in-vitro cytotoxicity against THP-1, COLO-205, HCT-116 and A-549 human cancer cell lines. The results indicated that 2a, 3a, 5a and 6a possessed significant

  本研究涉及作为约束查尔酮类似物的一系列3-芳基-9-乙酰基-哒嗪并[3,4-b]吲哚的设计。提出了用于目标化合物合成的逆合成途径。评价所有合成的化合物对THP-1，COLO-205，HCT-116和A-549人癌细胞系的体外细胞毒性。结果表明2a，3a，5a和6a具有明显的细胞毒性潜力，IC 50值范围为1.13至5.76μM。结构活性关系表明，环A和环B的性质都会影响其活性。发现苯环上的甲氧基（环A）和未取代的苯环上的取代（环B）是优选的结构特征。进一步测试了最有效的化合物2a对微管蛋白的抑制作用。发现化合物2a显着抑制微管蛋白聚合（针对THP-1的IC 50值为– 2.41μM）。如免疫荧光技术所证明，化合物2a还引起微管装配的破坏。2a具有明显的细胞毒性和微管蛋白抑制作用通过分子模型研究合理化。最有效的结构停靠在秋水仙碱结合位点（PDB ID-1SA0），并发现它通过各种疏水和氢键相互作用在空腔中稳定。
• Synthesis of novel oxindolylpyrrolo[2,3-d]pyrimidines via a three-component sequential tandem reaction
  作者：Kurosh Rad-Moghadam、Seyyedeh Cobra Azimi

  DOI：10.1016/j.tet.2012.09.045

  日期：2012.11

  A novel one-pot three-component reaction of 6-amino-uracil, isatin, and acetophenone was accomplished through a programmed pH variation for the synthesis of 5-(2-oxoindolin-3-yl)-1H-pyrrolo[2,3-d]pyrimidine-2,4(3H,7H)-dione derivatives. The reaction was conducted in a sequential tandem manner to give the oxindole substituted pyrrolo[2,3-d]pyrimidine products in good to excellent yields. Despite of

  通过程序设定的pH值变化，可以合成5-（2-氧代吲哚-3-基）-1 H-吡咯并完成6-氨基尿嘧啶，靛红和乙酰苯的新型一锅三组分反应[2， 3 - d ]嘧啶-2,4（3 H，7 H）-二酮衍生物。以顺序串联方式进行反应，以良好至极好的收率得到羟吲哚取代的吡咯并[2，3- d ]嘧啶产物。尽管有时间安排，但所有过程都在一个锅中进行。这些新型化合物中的大多数在体外均显示出窄至良好的抗菌活性谱。
• Ordered short channel mesoporous silica modified with 1,3,5-triazine–piperazine as a versatile recyclable basic catalyst for cross-aldol, Knoevenagel and conjugate addition reactions with isatins
  作者：Naveen Gupta、Tamal Roy、Debashis Ghosh、Sayed H. R. Abdi、Rukhsana I. Kureshy、Noor-ul H. Khan、Hari C. Bajaj

  DOI：10.1039/c5ra00406c

  日期：——

  A recyclable triazine–piperazine immobilized silica supported material was explored as a heterogeneous catalyst for indole skeletal synthesized from isatins at RT.

  一种可回收的三嗪-哌嗪固定在硅胶支撑材料上的材料被探索作为在室温下从异吲哚酮合成的杂环骨架的非均相催化剂。
• Synthesis and biological evaluation of spiro[cyclopropane-1,3′-indolin]-2′-ones as potential anticancer agents
  作者：Chada Narsimha Reddy、V. Lakshma Nayak、Geeta Sai Mani、Jeevak Sopanrao Kapure、Praveen Reddy Adiyala、Ram Awatar Maurya、Ahmed Kamal

  DOI：10.1016/j.bmcl.2015.08.056

  日期：2015.10

  Libraries of spiro[cyclopropane-1,3'-indolin]-2'-ones were synthesized and evaluated for their biological activity against five different human cancer cell lines HT-29 (colon cancer), DU-145 (prostate cancer), Hela (cervical cancer), A-549 (Lung cancer), and MCF-7 (breast cancer). Many compounds of the series exhibited promising anticancer activity (IC50 < 20 mu M) against the studied cell lines. Based on the screening results, a structure activity relationship (SAR) of the pharmacophore was proposed. Among the series compound 6b and 6u showed significant activity against human prostate cancer cell line, DU-145. Flow cytometric analysis showed that these two compounds arrested the cell cycle in the G0/G1 phase leading to caspase-3 dependent apoptotic cell death. Further, measurement of mitochondrial membrane potential and Annexin V-FITC assay also suggested that 6b and 6u induced cell death by apoptosis. (C) 2015 Elsevier Ltd. All rights reserved.
• Design, synthesis and insilico studies of 3-fluoro-3-substituted oxindoles against cancer targets
  作者：P.L.N. Ranganath、A. Venkat Narsaiah

  DOI：10.1016/j.jfluchem.2023.110134

  日期：2023.5

  substituted isatins were subjected to Aldol condensation with various ketones. The resulted 3-hydroxy compounds were transformed into fluorine derivatives. Thus obtained, 3-fluoro-3-substituted oxindoles were screened for Insilco evaluation against anti-cancer targets VEGFR2 and GSK-3β. The study reveals that the fluoro compounds showed binding at their active sites. Particularly, compounds 4i, 4n and

  靛红和取代的靛红经过与各种酮的羟醛缩合。将所得的 3-羟基化合物转化为氟衍生物。由此获得的 3-fluoro-3-substituted oxindoles 被筛选用于针对抗癌靶标 VEGFR2 和 GSK-3β 的 Insilco 评估。该研究表明，氟化合物在其活性位点显示出结合。特别是，化合物4i、4n和4q显示出最好的结合亲和力和与它们各自的共结晶配体相似的疏水相互作用。