3,2'-dioxo-1,3,1',2'-tetrahydro-[2,3']biindolylidene-5'-sodium sulfonate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3,2'-dioxo-1,3,1',2'-tetrahydro-[2,3']biindolylidene-5'-sodium sulfonate
• 英文别名: sodium;(3Z)-2-oxo-3-(3-oxo-1H-indol-2-ylidene)-1H-indole-5-sulfonate
• 化学式: C₁₆H₉N₂O₅S*Na
• 分子量: 364.314
• InChiKey: BLRNJLBNCQORPO-HPWRNOGASA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.43
• 重原子数：
  25.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  115.4
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3,2'-dioxo-1,3,1',2'-tetrahydro-[2,3']biindolylidene-5'-sodium sulfonate 在 吡啶 、 盐酸羟胺 作用下， 以30%的产率得到indirubin-3'-oxime-5-sulfonic acid sodium salt
  参考文献：
  名称：

  Synthesis and structure–activity relationships of novel indirubin derivatives as potent anti-proliferative agents with CDK2 inhibitory activities

  摘要：

  Indirubin, an active ingredient of a traditional Chinese recipe Danggui Loughui Wan, has been known as it CDK inhibitor competing with ATP for binding to the catalytic site of cyclin-dependent kinases (CDKs). Since CDKs, a group of serine/ threonine kinases forming active heterodimeric complexes with cyclins, are key regulators of the cell cycle regulation, therapeutic interventions targeting CDKs have been stimulated for the treatment of proliferative diseases, such as cancer, psoriasis, and for the prevention of chemotherapy-associated side effects, Such its alopecia. A series of novel indirubin analogs was synthesized and evaluated for anti-proliferative and CDK2 inhibitory activities. Among the indirubin derivatives tested in the growth inhibitions against several human cancer cell lines, 5-nitro, halide, and bulky group Containing acylamino Substituted analogs showed high anti-proliferative effects. Selected analogs showing potent anti-proliferative activities were evaluated further in the CDK2 enzyme assay, Which resulted in the discovery of potent CDK2 inhibitors. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.08.008
• 作为产物：
  描述：

  吲哚乙酸酯 、 5-isatinsulfonic acid sodium salt 在 sodium carbonate 作用下， 以 甲醇 为溶剂， 生成 3,2'-dioxo-1,3,1',2'-tetrahydro-[2,3']biindolylidene-5'-sodium sulfonate
  参考文献：
  名称：

  Synthesis and structure–activity relationships of novel indirubin derivatives as potent anti-proliferative agents with CDK2 inhibitory activities

  摘要：

  Indirubin, an active ingredient of a traditional Chinese recipe Danggui Loughui Wan, has been known as it CDK inhibitor competing with ATP for binding to the catalytic site of cyclin-dependent kinases (CDKs). Since CDKs, a group of serine/ threonine kinases forming active heterodimeric complexes with cyclins, are key regulators of the cell cycle regulation, therapeutic interventions targeting CDKs have been stimulated for the treatment of proliferative diseases, such as cancer, psoriasis, and for the prevention of chemotherapy-associated side effects, Such its alopecia. A series of novel indirubin analogs was synthesized and evaluated for anti-proliferative and CDK2 inhibitory activities. Among the indirubin derivatives tested in the growth inhibitions against several human cancer cell lines, 5-nitro, halide, and bulky group Containing acylamino Substituted analogs showed high anti-proliferative effects. Selected analogs showing potent anti-proliferative activities were evaluated further in the CDK2 enzyme assay, Which resulted in the discovery of potent CDK2 inhibitors. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.08.008

文献信息

• Enhancing effect of indirubin derivatives on 1,25-dihydroxyvitamin D3- and all-trans retinoic acid-induced differentiation of HL-60 leukemia cells
  作者：Seung Hyun Kim、Si-Wouk Kim、Soo Jeong Choi、Yong-Chul Kim、Tae Sung Kim

  DOI：10.1016/j.bmc.2006.05.044

  日期：2006.10

  The induction of differentiation represents a new and promising approach to cancer therapy, well illustrated by the treatment of acute promyelocytic leukemia (APL) with 1,25-dihydroxyvitamin D-3 [1,25-(OH)(2)D-3] or all-trans retinoic acid (ATRA). Using combinations of low, nontoxic concentrations of either 1,25-(OH)(2)D-3 or ATRA and differentiation-enhancing chemicals, adverse effects such as hypercalcemic effects have been ameliorated, and long-term survival has been improved. Indirubin has been demonstrated to exert anti-leukemic effects in cases of chronic myclocytic leukemia. Previously, we synthesized a series of indirubin derivatives and evaluated their anti-proliferative properties against cancer cells. In this study, we determined the enhancing activities of these derivatives on 1,25-(OH)(2)D-3- and ATRA-induced differentiation of human promyelocytic leukemia HL-60 cells. Importantly, some of these derivatives were found to synergistically enhance the differentiation of HL-60 cells in a concentration-dependent manner when coupled with low doses of either 1,25-(OH)(2)D-3 or ATRA. The ability of indirubin derivatives to enhance the differentiation potential of 1,25(OH)(2)D-3 or ATRA may improve the ultimate outcomes of APL therapy. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis and structure–activity relationships of novel indirubin derivatives as potent anti-proliferative agents with CDK2 inhibitory activities
  作者：Myoung Ju Moon、Sang Kook Lee、Jong-Won Lee、Woo Keun Song、Si Wouk Kim、Jae Il Kim、Chunghee Cho、Soo Jeong Choi、Yong-Chul Kim

  DOI：10.1016/j.bmc.2005.08.008

  日期：2006.1

  Indirubin, an active ingredient of a traditional Chinese recipe Danggui Loughui Wan, has been known as it CDK inhibitor competing with ATP for binding to the catalytic site of cyclin-dependent kinases (CDKs). Since CDKs, a group of serine/ threonine kinases forming active heterodimeric complexes with cyclins, are key regulators of the cell cycle regulation, therapeutic interventions targeting CDKs have been stimulated for the treatment of proliferative diseases, such as cancer, psoriasis, and for the prevention of chemotherapy-associated side effects, Such its alopecia. A series of novel indirubin analogs was synthesized and evaluated for anti-proliferative and CDK2 inhibitory activities. Among the indirubin derivatives tested in the growth inhibitions against several human cancer cell lines, 5-nitro, halide, and bulky group Containing acylamino Substituted analogs showed high anti-proliferative effects. Selected analogs showing potent anti-proliferative activities were evaluated further in the CDK2 enzyme assay, Which resulted in the discovery of potent CDK2 inhibitors. (c) 2005 Elsevier Ltd. All rights reserved.