1-[2-氧代-2-(噻吩-3-基)乙基]吡啶碘化物 | 1030917-93-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-[2-氧代-2-(噻吩-3-基)乙基]吡啶碘化物
• 英文名称: 1-[2-oxo-2-(thiophen-3-yl)ethyl]pyridinium iodide
• 英文别名: 2-Pyridin-1-ium-1-yl-1-thiophen-3-ylethanone;iodide
• CAS: 1030917-93-1
• 化学式: C₁₁H₁₀NOS*I
• 分子量: 331.177
• InChiKey: VXKLBTQVEZXXGC-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.08
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  49.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(furan-2-yl)-1-(thiophen-2-yl)prop-2-en-1-one 、 1-[2-氧代-2-(噻吩-3-基)乙基]吡啶碘化物 在 ammonium acetate 作用下， 以 甲醇 为溶剂， 生成 4-(Furan-2-yl)-2-thiophen-2-yl-6-thiophen-3-ylpyridine
  参考文献：
  名称：

  2,6-Dithienyl-4-furyl pyridines: Synthesis, topoisomerase I and II inhibition, cytotoxicity, structure–activity relationship, and docking study

  摘要：

  For the development of novel antitumor agents, 2,6-dithienyl-4-furyl pyridine derivatives were prepared and evaluated for their topoisomerase I and II inhibitory activity as well as cytotoxicity against several human cancer cell lines. Among the 21 prepared compounds, compound 24 exhibited strong topoisomerase I inhibitory activity. In addition, a docking study with topoisomerase I and compound 24 was performed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.11.041
• 作为产物：
  描述：

  吡啶 、 3-乙酰基噻吩 在 碘 作用下， 以100%的产率得到1-[2-氧代-2-(噻吩-3-基)乙基]吡啶碘化物
  参考文献：
  名称：

  作为拓扑异构酶II抑制剂和细胞毒性剂的2-苯酚-4-氯苯基-6-芳基吡啶的合成和生物学评估。

  摘要：

  设计，合成并合成了一系列新的2-苯酚-4-氯苯基-6-芳基吡啶，并评估了其对拓扑异构酶（topo）I和II的抑制活性以及对四种不同的人类癌细胞系（例如HCT15，T47D）的细胞毒活性，DU145和Hela。与依托泊苷相比，大多数被测化合物在100μM处表现出更强的topo II抑制活性。除39种化合物外，所有化合物均未显示topo I抑制活性。有趣的是，显示出比依托泊苷更好的topo II抑制作用的化合物在中央吡啶的4位具有邻-或对-氯苯基，并且没有一个化合物具有间-氯苯基。SAR研究表明，中央吡啶4位上的邻氯苯基或对氯苯基对于选择性的topo II抑制活性很重要。相似地，所有具有间羟基或对羟基苯基部分的化合物均显示出中度至显着的细胞毒性作用。特别是，对T47D乳腺癌细胞显示出优异细胞毒性（IC50 =0.68-1.25μM）的化合物27-37和39表明，在中央吡啶2位上的间位或对位羟基

  DOI：

  10.1016/j.bioorg.2016.04.007

文献信息

• Design and synthesis of novel 2,4-diaryl-5H-indeno[1,2-b]pyridine derivatives, and their evaluation of topoisomerase inhibitory activity and cytotoxicity
  作者：Tara Man Kadayat、Chanmi Park、Kyu-Yeon Jun、Til Bahadur Thapa Magar、Ganesh Bist、Han Young Yoo、Youngjoo Kwon、Eung-Seok Lee

  DOI：10.1016/j.bmc.2014.11.010

  日期：2015.1

  topoisomerase II inhibitory activity. Compounds 7, 8, 11, 12, 13, and 22 with 2-furyl, 2-thienyl or 3-thienyl at 2-position of central pyridine showed the significant or moderate topoisomerase I inhibitory activity. Especially, compound 12 with strong topoisomerase II inhibitory activity at 100 μM and 20 μM, and moderate topoisomerase I inhibitory activity displayed strong cytotoxicity against several

  为了开发潜在的抗癌药，我们设计和合成了30种新的2,4-二芳基-5 H-茚并[1,2- b ]吡啶衍生物，其在2-和-3处含有芳基部分，例如呋喃基，噻吩基，吡啶基和苯基。 5 H-茚并[1,2- b ]吡啶的4位。他们评估了拓扑异构酶I和II的抑制活性，以及​​对几种人类癌细胞系的细胞毒性。中制备的30种化合物，7，8，9，10，12，14，16，19，20，22，和23在中央吡啶的2-或4-位上的2-或3-呋喃基和/或2-或3-噻吩基具有明显或中等的拓扑异构酶II抑制活性。化合物7，8，11，12，13，和22与2-呋喃基，2-噻吩基或在中央吡啶2-位3-噻吩基显示显著或中度拓扑异构酶I抑制活性。尤其是，化合物12在100μM和20μM时具有强大的拓扑异构酶II抑制活性，而中等的拓扑异构酶I抑制活性则表现出对几种人类癌细胞系的强大细胞毒性。
• Synthesis of 2,6-diaryl-substituted pyridines and their antitumor activities
  作者：Jong-Keun Son、Long-Xuan Zhao、Arjun Basnet、Pritam Thapa、Radha Karki、Younghwa Na、Yurngdong Jahng、Tae Cheon Jeong、Byeong-Seon Jeong、Chong-Soon Lee、Eung-Seok Lee

  DOI：10.1016/j.ejmech.2007.05.002

  日期：2008.4

  For the development of novel antitumor agents, we designed and synthesized 2,6-diaryl-substituted pyridine derivatives bearing three aryl groups, which are the bioisosteres of terpyridine, and evaluated their biological activities. Most of the 18 prepared compounds showed moderate cytotoxicity against several human cancer cell lines. From the structure-activity relationships we may conclude that the number of aryl groups employed would be critical for their biological activities. (c) 2007 Elsevier Masson SAS. All rights reserved.
• Synthesis of 2,4-diaryl chromenopyridines and evaluation of their topoisomerase I and II inhibitory activity, cytotoxicity, and structure–activity relationship
  作者：Uttam Thapa、Pritam Thapa、Radha Karki、Minho Yun、Jae Hun Choi、Yurngdong Jahng、Eunyoung Lee、Kyung-Hwa Jeon、Younghwa Na、Eun-Mi Ha、Won-Jea Cho、Youngjoo Kwon、Eung-Seok Lee

  DOI：10.1016/j.ejmech.2011.04.029

  日期：2011.8

  Designed and synthesized were a series of 5H-chromeno[4,3-b]pyridines with substitution at 2- and 4-positions with various 5- or 6-membered heteroaromatics as antitumor agents. They were evaluated for topoisomerase I and II inhibitory activities as well as cytotoxicities against several human cancer cell lines. Structure activity relationship study showed that 2-furyl or 2-thienyl at 2- or 4-position of central pyridine is crucial in displaying topo I or II inhibitory activity and cytotoxicity. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Synthesis, topoisomerase I and II inhibitory activity, cytotoxicity, and structure–activity relationship study of hydroxylated 2,4-diphenyl-6-aryl pyridines
  作者：Radha Karki、Pritam Thapa、Mi Jeong Kang、Tae Cheon Jeong、Jung Min Nam、Hye-Lin Kim、Younghwa Na、Won-Jea Cho、Youngjoo Kwon、Eung-Seok Lee

  DOI：10.1016/j.bmc.2010.03.051

  日期：2010.5

  A new series of 2,4-diphenyl-6-aryl pyridines containing hydroxyl group(s) at the ortho, meta, or para position of the phenyl ring were synthesized, and evaluated for topoisomerase I and II inhibitory activity and cytotoxicity against several human cancer cell lines for the development of novel anticancer agents. Structure-activity relationship study revealed that the substitution of hydroxyl group( s) increased topoisomerase I and II inhibitory activity in the order of meta > para > ortho position. Substitution of hydroxyl group on the para position showed better cytotoxicity. (c) 2010 Elsevier Ltd. All rights reserved.
• Design, synthesis, and antitumor evaluation of 2,4,6-triaryl pyridines containing chlorophenyl and phenolic moiety
  作者：Pritam Thapa、Radha Karki、Minho Yun、Tara Man Kadayat、Eunyoung Lee、Han Byeol Kwon、Younghwa Na、Won-Jea Cho、Nam Doo Kim、Byeong-Seon Jeong、Youngjoo Kwon、Eung-Seok Lee

  DOI：10.1016/j.ejmech.2012.03.010

  日期：2012.6

  We have designed and synthesized a series of 2,4,6-triaryl pyridine derivatives containing chlorophenyl and phenolic moeity at 2- and 4- position of the central pyridine, respectively, resulting in a total of 42 compounds. They were evaluated for topoisomerase I and 11 inhibitory activities as well as cytotoxicities against several human cancer cell lines. Most compounds showed better topoisomerase II inhibitory activity compared to topoisomerase 1 inhibitory activity. Compounds 19, 20, 26-28, and 47-50 especially showed stronger topo II inhibitory activity than etoposide. (C) 2012 Elsevier Masson SAS. All rights reserved.