1-(4-hydroxy-phenacyl)pyridinium; iodide

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-hydroxy-phenacyl)pyridinium; iodide
• 英文别名: 1-(4-Hydroxy-phenacyl)pyridinium; Jodid；1-(4-Hydroxyphenyl)-2-pyridin-1-ium-1-ylethanone;iodide
• 化学式: C₁₃H₁₂NO₂*I
• 分子量: 341.148
• InChiKey: GGFMLIYIIBMFLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.43
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  41.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-hydroxy-phenacyl)pyridinium; iodide 在 sodium hydroxide 作用下， 生成 对羟基苯甲酸
  参考文献：
  名称：

  The congenital chloride diarrhea gene is expressed in seminal vesicle, sweat gland, inflammatory colon epithelium, and in some dysplastic colon cells

  摘要：

  Congenital chloride diarrhea (CLD) is an autosomal recessive disorder of intestinal electrolyte transportation caused by mutations in the anion transporter protein encoded by the down-regulated in adenoma (DRA), or CLD, gene. In this study, in situ hybridization and immunohistochemistry were performed to investigate the expression of CLD in extraintestinal normal epithelia and in intestinal inflammatory and neoplastic epithelia. The expression of the closely related anion transporter diastrophic dysplasia sulfate transporter, DTDST, was also examined and compared with that of CLD in colon. The only extraintestinal tissues showing CLD expression were eccrine sweat Elands and seminal vesicles. In inflammatory bowel disease and ischemic colitis, expression of CLD mRNA in colon epithelium was similar to histologically normal colon epithelium, but the protein was found deeper in crypts, including proliferative epithelial cells. In intestinal tumors, the expression pattern of CLD was dependent on the differentiation status of the tissue studied: epithelial polyps with no or minor dysplasia showed abundant expression, whereas adenocarcinomas were negative. The DTDST gene was abundantly expressed in the upper crypt epithelium of colonic mucosa.

  DOI：

  10.1007/s004180000131
• 作为产物：
  描述：

  吡啶 、 对羟基苯乙酮 在 碘 作用下， 反应 3.0h， 生成 1-(4-hydroxy-phenacyl)pyridinium; iodide
  参考文献：
  名称：

  2-苯基或羟基化的2-苯基-4-芳基-5 H-茚并[1,2- b ]吡啶的合成，拓扑异构酶I和II的抑制活性，细胞毒性和结构-活性关系的研究

  摘要：

  合成了一系列新颖的二十八个刚性的2​​-苯基或羟基化的2-苯基-4-芳基-5 H-茚并[1,2- b ]吡啶，并对其拓扑异构酶抑制活性以及对几种化合物的细胞毒性进行了评估。人类癌细胞系。通常，羟基化的化合物（16 - 18，22 - 25，和29 - 31）在中央吡啶的4位上含有呋喃基或噻吩基部分的化合物在低微摩尔范围内分别与阳性对照，喜树碱和依托泊苷相比，表现出较强的拓扑异构酶I和II抑制活性。结构-活性关系研究表明，在2-苯环上带有羟基的茚并吡啶化合物与在4-位上的呋喃基或噻吩基部分结合在一起对拓扑异构酶的抑制很重要。化合物（22 - 25），其含有羟基的间位以2位和呋喃基或在indenopyridine的4-位噻吩基取代的2-苯基环的位置，显示之间拓扑异构酶I和II的抑制活性，和细胞毒性对评价具体的相关性人类癌细胞系。

  DOI：

  10.1016/j.bmc.2015.04.031

文献信息

• Synthesis, topoisomerase I and II inhibitory activity, cytotoxicity, and structure–activity relationship study of 2-phenyl- or hydroxylated 2-phenyl-4-aryl-5H-indeno[1,2-b]pyridines
  作者：Tara Man Kadayat、Chanju Song、Somin Shin、Til Bahadur Thapa Magar、Ganesh Bist、Aarajana Shrestha、Pritam Thapa、Younghwa Na、Youngjoo Kwon、Eung-Seok Lee

  DOI：10.1016/j.bmc.2015.04.031

  日期：2015.7

  topoisomerase I and II inhibitory activity compared to positive control, camptothecin and etoposide, respectively, in low micromolar range. Structure–activity relationship study revealed that indenopyridine compounds with hydroxyl group at 2-phenyl ring in combination with furyl or thienyl moiety at 4-position are important for topoisomerase inhibition. Compounds (22–25) which contain hydroxyl group at

  合成了一系列新颖的二十八个刚性的2​​-苯基或羟基化的2-苯基-4-芳基-5 H-茚并[1,2- b ]吡啶，并对其拓扑异构酶抑制活性以及对几种化合物的细胞毒性进行了评估。人类癌细胞系。通常，羟基化的化合物（16 - 18，22 - 25，和29 - 31）在中央吡啶的4位上含有呋喃基或噻吩基部分的化合物在低微摩尔范围内分别与阳性对照，喜树碱和依托泊苷相比，表现出较强的拓扑异构酶I和II抑制活性。结构-活性关系研究表明，在2-苯环上带有羟基的茚并吡啶化合物与在4-位上的呋喃基或噻吩基部分结合在一起对拓扑异构酶的抑制很重要。化合物（22 - 25），其含有羟基的间位以2位和呋喃基或在indenopyridine的4-位噻吩基取代的2-苯基环的位置，显示之间拓扑异构酶I和II的抑制活性，和细胞毒性对评价具体的相关性人类癌细胞系。
• Design, synthesis, and structure-activity relationships of new benzofuro[3,2-b]pyridin-7-ols as DNA topoisomerase II inhibitors
  作者：Aarajana Shrestha、Hyunji Jo、Youngjoo Kwon、Eung-Seok Lee

  DOI：10.1016/j.bmcl.2018.01.048

  日期：2018.2

  drugs. In this study, a series of new benzofuro[3,2-b]pyridin-7-ols were designed and synthesized for the first time and screened for their topoisomerase I and II inhibitory and antiproliferative activity. Structure-activity relationships revealed the position of ortho- and para-hydroxyl group at 2-phenyl ring, and meta-hydroxyl group at 4-phenyl ring of benzofuro[3,2-b]pyridin-7-ol are important for potent

  人类DNA拓扑异构酶已成为开发更有效的抗癌药物的诱人靶标。在这项研究中，首次设计和合成了一系列新的苯并呋喃[3,2 - b ]吡啶-7-ol，并筛选了它们对拓扑异构酶I和II的抑制和抗增殖活性。构效关系揭示了苯并呋喃[3,2 - b ]吡啶-7-ol在2-苯基环上的邻羟基和对羟基位置以及在4-苯基环上的间羟基对于有效的和重要的活性很重要。选择性的topo II抑制活性。化合物11表现出最具选择性和效力的topo II抑制作用（在100 µM时抑制100％）和最强的抗增殖活性（IC50  = 0.86 µM）。
• Dihydroxylated 2,6-diphenyl-4-chlorophenylpyridines: Topoisomerase I and IIα dual inhibitors with DNA non-intercalative catalytic activity
  作者：Ganesh Bist、Seojeong Park、Chanju Song、Til Bahadur Thapa Magar、Aarajana Shrestha、Youngjoo Kwon、Eung-Seok Lee

  DOI：10.1016/j.ejmech.2017.03.048

  日期：2017.6

  structure-activity relationship study revealed that the para position of a hydroxyl group at 2-and 6-phenyl ring and chlorine atom at the para position of 4-phenyl ring of the central pyridine exhibited the most significant topo I and topo IIα inhibition, which might indicate introduction of the chlorine atom at the phenyl ring of 4-pyridine have an important role as dual inhibitors of topo I and topo IIα

  为了开发新型的抗增殖药，系统设计，制备和研究了一系列新的十八种二羟基化的2,6-二苯基-4-氯苯基吡啶，并研究了它们对三种异构体的拓扑异构酶（拓扑）I和IIα的抑制特性和抗增殖作用癌细胞系（HCT15，T47D和HeLa）。在中央吡啶环的2-或6-位上具有间-或对-苯酚的化合物22-30显示出显着的双重topo I和topoIIα抑制活性，并对所有测试的人类癌细胞系具有强的抗增殖活性。但是，化合物13-21在2-上具有邻苯酚，中央吡啶环的6-位或6-位未显示出明显的topo I和topoIIα抑制活性，但显示出对所有测试的人类癌细胞系的中等抗增殖活性。在T47D癌细胞系中，与依托泊苷和喜树碱相比，化合物23表现出最高的抗增殖效能，分别高达348.5和105倍。构效关系研究表明，中央吡啶的2-和6-苯环上的羟基的对位和中心吡啶上的氯原子在4-苯环上的对位表现出最显着的topo I和topoI
• Modified 2,4-diaryl-5H-indeno[1,2-b]pyridines with hydroxyl and chlorine moiety: Synthesis, anticancer activity, and structure–activity relationship study
  作者：Tara Man Kadayat、Chanju Song、Youngjoo Kwon、Eung-Seok Lee

  DOI：10.1016/j.bioorg.2015.07.002

  日期：2015.10

  to the non-substituted 2,4-diaryl-5H-indeno[1,2-b]pyridines. Compounds (2, 3, 4, 5, 8, and 9) with meta or para hydroxyl group on 2 or 4-phenyl ring have enhanced topo I and II inhibitory activity and cytotoxicity. However, additional substitution of chlorine group on furyl or thienyl ring (11, 12, 14, 16–18) generally reduced topo I and II inhibitory activity but improved cytotoxicity. The observation

  作为开发新型抗癌剂的正在进行研究的一部分，设计了一系列修饰的2,4-二芳基-5 H-茚并[1,2- b ]吡啶，并通过引入羟基和氯部分进行合成。对它们的拓扑异构酶抑制活性和针对HCT15，T47D和HeLa癌细胞系的细胞毒性进行了评估。这种修饰使我们能够证明有关非取代的2,4-二芳基-5 H-茚并[1,2- b ]吡啶的结构-活性关系（SAR）研究。化合物（2，3，4，5，8，和9）与间位或对位2或4-苯环上的羟基具有增强的topo I和II抑制活性和细胞毒性。然而，呋喃基或噻吩环（氯基的额外替代11，12，14，16-18）通常会降低拓扑异构酶I和II的抑制活性，但改善的细胞毒性。根据羟基和氯基的位置观察细胞毒性和进行SAR研究，将为进一步研究具有相关支架的新型抗癌药提供有价值的见识。
• Effect of chlorine substituent on cytotoxic activities: Design and synthesis of systematically modified 2,4-diphenyl-5H-indeno[1,2-b]pyridines
  作者：Tara Man Kadayat、Seojeong Park、Kyu-Yeon Jun、Til Bahadur Thapa Magar、Ganesh Bist、Aarajana Shrestha、Younghwa Na、Youngjoo Kwon、Eung-Seok Lee

  DOI：10.1016/j.bmcl.2016.02.053

  日期：2016.4

  4-phenyl ring. Eighteen new chlorinated compounds were thus prepared and assessed for topoisomerase inhibitory activity and cytotoxicity against HCT15, T47D, and HeLa cancer cell lines. All of the chlorinated compounds displayed significant cytotoxic effect, revealing potent anticancer activity against T47D breast cancer cells. This functional group modification allowed us to explore the importance of

  在继续我们先前的工作时，通过在邻位，间位或对位引入一个氯官能团，对六个羟基化的2,4-二苯基-5 H-茚并[1,2- b ]吡啶类似物进行了修饰2-或4-苯基环的位置。因此，制备了十八种新的氯化化合物，并评估了其对HCT15，T47D和HeLa癌细胞株的拓扑异构酶抑制活性和细胞毒性。所有含氯化合物均显示出显着的细胞毒性作用，显示出针对T47D乳腺癌细胞的有效抗癌活性。这种官能团的修饰使我们能够探索氯基取代对细胞毒性特性的重要性。本文报道的信息为进一步研究使用相关支架开发新的抗癌药物提供了宝贵的见识。