5-(4-carbamoylphenyl)methylene-3-[4-(3-diethylaminopropoxy)phenyl]-2-thioxo-4-thiazolidinone | 1394355-24-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(4-carbamoylphenyl)methylene-3-[4-(3-diethylaminopropoxy)phenyl]-2-thioxo-4-thiazolidinone
• 英文别名: 4-[[3-[4-[3-(Diethylamino)propoxy]phenyl]-4-oxo-2-sulfanylidene-1,3-thiazolidin-5-ylidene]methyl]benzamide；4-[[3-[4-[3-(diethylamino)propoxy]phenyl]-4-oxo-2-sulfanylidene-1,3-thiazolidin-5-ylidene]methyl]benzamide
• CAS: 1394355-24-8
• 化学式: C₂₄H₂₇N₃O₃S₂
• 分子量: 469.629
• InChiKey: WBCAMLIYXWYHKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  133
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N,N-diethyl-3-(4-nitrophenoxy)propan-1-amine 在 palladium 10% on activated carbon 、 氢气 、 sodium acetate 作用下， 以 甲醇 、 乙醇 、 水 、 溶剂黄146 为溶剂， 生成 5-(4-carbamoylphenyl)methylene-3-[4-(3-diethylaminopropoxy)phenyl]-2-thioxo-4-thiazolidinone
  参考文献：
  名称：

  Discovery of potent and selective rhodanine type IKKβ inhibitors by hit-to-lead strategy

  摘要：

  Regulation of NF-kappa B activation through the inhibition of IKK beta has been identified as a promising target for the treatment of inflammatory and autoimmune disease such as rheumatoid arthritis. In order to develop novel IKK beta inhibitors, we performed high throughput screening toward around 8000 library compounds, and identified a hit compound containing rhodanine moiety. We modified the structure of hit compound to obtain potent and selective IKK beta inhibitors. Throughout hit-to-lead studies, we have discovered optimized compounds which possess blocking effect toward NF-kappa B activation and TNF alpha production in cell as well as inhibition activity against IKK beta. Among them, compound 3q showed the potent inhibitory activity against IKK beta, and excellent selectivity over other kinases such as p38 alpha, p38 beta, JNK1, JNK2, and JNK3 as well as IKK alpha. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.088

文献信息

• Discovery of potent and selective rhodanine type IKKβ inhibitors by hit-to-lead strategy
  作者：Hyeseung Song、Yun Suk Lee、Eun Joo Roh、Jae Hong Seo、Kwang-Seok Oh、Byung Ho Lee、Hogyu Han、Kye Jung Shin

  DOI：10.1016/j.bmcl.2012.06.088

  日期：2012.9

  Regulation of NF-kappa B activation through the inhibition of IKK beta has been identified as a promising target for the treatment of inflammatory and autoimmune disease such as rheumatoid arthritis. In order to develop novel IKK beta inhibitors, we performed high throughput screening toward around 8000 library compounds, and identified a hit compound containing rhodanine moiety. We modified the structure of hit compound to obtain potent and selective IKK beta inhibitors. Throughout hit-to-lead studies, we have discovered optimized compounds which possess blocking effect toward NF-kappa B activation and TNF alpha production in cell as well as inhibition activity against IKK beta. Among them, compound 3q showed the potent inhibitory activity against IKK beta, and excellent selectivity over other kinases such as p38 alpha, p38 beta, JNK1, JNK2, and JNK3 as well as IKK alpha. (C) 2012 Elsevier Ltd. All rights reserved.