3-(3-(diethylamino)propyl)-2-thioxothiazolidin-4-one | 21414-00-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 3-(3-(diethylamino)propyl)-2-thioxothiazolidin-4-one
• 英文别名: 3-<3-(Diethylamino)propyl>rhodanin；3-(3-(diethylamino)propyl)-2-thioxo-4-thiazolidinone；3-[3-(Diethylamino)propyl]-2-sulfanylidene-1,3-thiazolidin-4-one
• CAS: 21414-00-6
• 化学式: C₁₀H₁₈N₂OS₂
• 分子量: 246.398
• InChiKey: KNAVDIBAAXNBRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  80.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(3-(diethylamino)propyl)-2-thioxothiazolidin-4-one 在 哌啶 、 三氟化硼乙醚 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel 4-thiazolidinones containing indolin-2-one moiety as potential antitumor agent

  摘要：

  A series of novel 4-thiazolidinone and indolin-2-one hybrid derivatives 5a-5s and 10a-10s have been designed and synthesized and their cytotoxic activities were evaluated in vitro against three human cancer cell lines including HT-29 (human colon cancer), H460 (human lung cancer), MDA-MB-231 (human breast cancer) by MTT assay. Several potent target compounds (5m, 5p, 5s, 10a, 10c-10g, 10m, 10p) were further evaluated against one cancer cell line SMMC-7721 (human liver cancer) and one normal cell line WI-38 (human fetal lung fibroblasts). Most of the prepared compounds exhibited significant antitumor activities against different human cancer cell lines. Compound 10c (IC50 = 0.025 mu M. 0.075 mu M, 0.77 mu M, 1.95 mu M) was 52, 36, 4.8 and 3.3 times more active than Sunitinib (IC50 = 1.3 mu M, 2.7 mu M, 3.7 mu M, 6.47 mu M) against HT-29, H460, MDA-MB-231 and SMMC-7721 cancer cell line, respectively. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.05.017
• 作为产物：
  描述：

  N-[3-(二乙基氨基)丙基]二硫代氨基甲酸 在 硫酸 、 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 12.0h， 生成 3-(3-(diethylamino)propyl)-2-thioxothiazolidin-4-one
  参考文献：
  名称：

  The interaction of 4-thiazolidinone derivatives containing indolin-2-one moiety with P-glycoprotein studied using K562 cell lines

  摘要：

  P-glycoprotein (P-gp) is an active drug efflux pump, which exists widely in various MDR tumor cells, conferring drug resistance to tumor cells during chemotherapy. Some 4-thiazolidinone derivatives containing indolin-2-one moiety are novel anti-tumor compounds. The aim of this study was to evaluate the transport activity of P-gp towards 4-thiazolidinone derivatives containing indolin-2-one moiety (as mixtures of 2Z, 5Z and 2E, 5Z isomers) and the transport inhibition activities of the derivatives to P-gp, the results of which could provide crucial information for the further separation of and development on the derivatives with excellent anti-tumor activities. The results indicate that the further separation and development should be focused on compounds 7, 10, 12 and 13 (tumor cell cytotoxic P-gp modulators) and compounds 8, 9, 17 and 18 (non-substrates of P-gp), which exhibit anti-tumor activities and could overcome P-gp mediated MDR. Furthermore, the results of molecular docking indicate that Ser222, a residue in TM4 domain of P-gp, exhibits an intriguing feature in that it interacts with all of the derivatives related with P-gp transport in a significant way, including both typical substrates and modulators of P-gp. Meanwhile, the compounds showing no interaction with Ser222 are mainly from the category of non-substrates of P-gp. Therefore, the interaction between Ser222 and the tested derivative would provide useful information for the further development on 4-thiazolidinone derivatives containing indolin-2-one moiety. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.06.002

文献信息

• 4-噻唑烷酮类衍生物及其应用
  申请人：沈阳药科大学

  公开号：CN104387378B

  公开（公告）日：2017-08-25

  本发明涉及通式Ⅰ所示的新的4‑噻唑烷酮衍生物、其几何异构体及其药学上可接受的盐，其中取代基R1、R2、R3、R4、n具有在说明书中给出的含义。本发明还涉及通式Ⅰ的化合物在制备治疗和/或预防癌症的药物中的用途。
• 페로브스카이트 제조용 화학첨가제 조성물, 이를 포함하는 페로브스카이트 및 페로브스카이트 태양전지
  申请人：UNIST(ULSAN NATIONAL INSTITUTE OF SCIENCE AND TECHNOLOGY) 울산과학기술원(120150812047) Corp. No ▼ 230171-0011595BRN ▼620-82-06236

  公开号：KR20200053266A

  公开（公告）日：2020-05-18

  본 발명은 반도체성 화합물을 포함하는 페로브스카이트 제조용 화학첨가제 조성물, 상기 화합물을 포함하는 페로브스카이트와 이의 제조방법 및 상기 페로브스카이트를 이용한 태양전지에 관한 것으로, 본 발명에 따른 화합물을 포함하는 페로브스카이트 제조용 화학첨가제 조성물은 온화한 조건에서 페로브스카이트 전구체 용액에 첨가되어 페로브스카이트 입자의 크기와 균일성을 향상된 고품질 페로브스카이트를 용이하게 제조할 수 있도록 하며, 상기 페로브스카이트 제조용 화학첨가제 조성물이 포함된 페로브스카이트를 이용하여 태양전지를 제조함으로써 태양전지의 안정성과 전력변환효율을 현저히 향상시킬 수 있다.

  本发明涉及一种用于制造钙钛矿材料的化学添加剂组合物，其中包含半导体化合物，以及包含该化合物的钙钛矿材料、其制备方法和使用该钙钛矿材料制造太阳能电池。根据本发明，包含该化合物的钙钛矿材料的化学添加剂组合物在温和条件下添加到钙钛矿前体溶液中，以便更容易地制造具有改善颗粒大小和均匀性的高品质钙钛矿材料。使用包含该钙钛矿材料制造太阳能电池可以显著提高太阳能电池的稳定性和功率转换效率。
• Design, synthesis and biological evaluation of novel 4-thiazolidinones containing indolin-2-one moiety as potential antitumor agent
  作者：Shuobing Wang、Yanfang Zhao、Guogang Zhang、Yingxiang Lv、Ning Zhang、Ping Gong

  DOI：10.1016/j.ejmech.2011.05.017

  日期：2011.8

  A series of novel 4-thiazolidinone and indolin-2-one hybrid derivatives 5a-5s and 10a-10s have been designed and synthesized and their cytotoxic activities were evaluated in vitro against three human cancer cell lines including HT-29 (human colon cancer), H460 (human lung cancer), MDA-MB-231 (human breast cancer) by MTT assay. Several potent target compounds (5m, 5p, 5s, 10a, 10c-10g, 10m, 10p) were further evaluated against one cancer cell line SMMC-7721 (human liver cancer) and one normal cell line WI-38 (human fetal lung fibroblasts). Most of the prepared compounds exhibited significant antitumor activities against different human cancer cell lines. Compound 10c (IC50 = 0.025 mu M. 0.075 mu M, 0.77 mu M, 1.95 mu M) was 52, 36, 4.8 and 3.3 times more active than Sunitinib (IC50 = 1.3 mu M, 2.7 mu M, 3.7 mu M, 6.47 mu M) against HT-29, H460, MDA-MB-231 and SMMC-7721 cancer cell line, respectively. (C) 2011 Elsevier Masson SAS. All rights reserved.
• The interaction of 4-thiazolidinone derivatives containing indolin-2-one moiety with P-glycoprotein studied using K562 cell lines
  作者：Feng Wang、Zijian Liu、Jian Wang、Jun Tao、Ping Gong、Xue Bao、Yanfang Zhao、Yulin Wang

  DOI：10.1016/j.ejmech.2015.06.002

  日期：2015.8

  P-glycoprotein (P-gp) is an active drug efflux pump, which exists widely in various MDR tumor cells, conferring drug resistance to tumor cells during chemotherapy. Some 4-thiazolidinone derivatives containing indolin-2-one moiety are novel anti-tumor compounds. The aim of this study was to evaluate the transport activity of P-gp towards 4-thiazolidinone derivatives containing indolin-2-one moiety (as mixtures of 2Z, 5Z and 2E, 5Z isomers) and the transport inhibition activities of the derivatives to P-gp, the results of which could provide crucial information for the further separation of and development on the derivatives with excellent anti-tumor activities. The results indicate that the further separation and development should be focused on compounds 7, 10, 12 and 13 (tumor cell cytotoxic P-gp modulators) and compounds 8, 9, 17 and 18 (non-substrates of P-gp), which exhibit anti-tumor activities and could overcome P-gp mediated MDR. Furthermore, the results of molecular docking indicate that Ser222, a residue in TM4 domain of P-gp, exhibits an intriguing feature in that it interacts with all of the derivatives related with P-gp transport in a significant way, including both typical substrates and modulators of P-gp. Meanwhile, the compounds showing no interaction with Ser222 are mainly from the category of non-substrates of P-gp. Therefore, the interaction between Ser222 and the tested derivative would provide useful information for the further development on 4-thiazolidinone derivatives containing indolin-2-one moiety. (C) 2015 Elsevier Masson SAS. All rights reserved.