selenophene-2-carbonyl chloride | 39082-07-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硒吩
• 英文名称: selenophene-2-carbonyl chloride
• CAS: 39082-07-0
• 化学式: C₅H₃ClOSe
• 分子量: 193.491
• InChiKey: ZHRDYPXQZUWHFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.12
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  selenophene-2-carbonyl chloride 在 iron(III) chloride 、 溶剂黄146 calcium borohydride 、 三氟化硼乙醚 、 lead(IV) tetraacetate 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 32.5h， 生成 1-phenyl-3-(5-hydroxymethyl-2-furyl)selenolo[3,2-c]pyrazole
  参考文献：
  名称：

  Selenolopyrazole derivatives and use thereof as anticancer agents

  摘要：

  本发明合成了一系列硒代[3,2-c]吡唑和硒代[2,3-c]吡唑衍生物，并发现它们的抗癌活性。

  公开号：

  US08053459B1
• 作为产物：
  描述：

  2-甲酰硒酚 在 sodium hydroxide 、 氯化亚砜 、 silver(l) oxide 作用下， 生成 selenophene-2-carbonyl chloride
  参考文献：
  名称：

  Chierici; Pappalardo, Gazzetta Chimica Italiana, 1958, vol. 88, p. 453,455

  摘要：

  DOI：

文献信息

• Heterocyclic-based ferrocenyl carboselenolates: Synthesis, solid-state structure and electrochemical investigations
  作者：Deeb Taher、Firas F. Awwadi、J. Matthäus Speck、Marcus Korb、Dieter Schaarschmidt、Saddam Weheabby、Almeqdad Y. Habashneh、Mousa Al-Noaimi、Mohammad El-Khateeb、Sultan T. Abu-Orabi、Heinrich Lang

  DOI：10.1016/j.jorganchem.2017.02.024

  日期：2017.9

  spectroscopy. The structures of 3a–c and 6a in the solid state were determined by single crystal X-ray structure analysis. The cyclic voltammetry measurements for 3a–c and 6a–c show reversible electrochemical processes (Fc/Fc+) between 135 and 170 mV for 3a−c and between 135 and 220 mV for 6a−c using [NnBu4][B(C6F5)4] as the supporting electrolyte. It was found that the furyl- and selenophyl-functionalized

  治疗两个当量。的的[Fe（η 5 -C 5 H ^ 5）（η 5 -C 5 H ^ 4 SeSiMe 3）]（1）与一种当量。2,5-（ClC（O））2 - c C 4 H 2 X（2）产生了相应的二茂铁基碳纤维烯酸酯2,5-[（FcSeC（O））2 - c C 4 H 2 X]（3） （[FC =铁（η 5 -C 5 H ^ 5）（η 5 -C5 H 4）]; a，X = O; b，X = NMe; c，X = Se）。在另一方面，的[Fe（η 5 -C 5 H ^ 4森达3）2 ]（4）与2- CLC（O）反应， - C ^ C ^ 4 ħ 3 X（5）以1：2 M比，得到的[Fe（η 5 -C 5 H ^ 4秒（O）-2- ç ç 4 ħ 3 X）2 ]（6） （一个，X = O; b，X = NMe; c，X = Se）。化合物3a – c和6a – c已通过元素分析，NMR（1 H，13
• Synthesis of 1-benzyl-3-(5-hydroxymethyl-2-furyl)selenolo[3,2-c]pyrazole derivatives as new anticancer agents
  作者：Li-Chen Chou、Li-Jiau Huang、Mei-Hua Hsu、Mei-Chi Fang、Jai-Sing Yang、Shi-Hong Zhuang、Hui-Yi Lin、Fang-Yu Lee、Che-Ming Teng、Sheng-Chu Kuo

  DOI：10.1016/j.ejmech.2009.12.039

  日期：2010.4

  As part of our continuing search for potential anticancer drug candidates among YC-1 analogs, 1, 3-disubstituted selenolo[3,2-c]pyrazole derivatives were synthesized and evaluated for their cytotoxicity against NCI-H226 non-small cell lung cancer and A-498 renal cancer cell lines. Significant cytotoxicity was observed in 3-(5-hydroxymethyl-2-furyl) derivatives (2, 33, 36 and 37). Among them, compound

  作为我们继续寻找YC-1类似物中潜在抗癌药物候选物的一部分，合成了1，3-双取代的硒代[3,2- c ]吡唑衍生物，并评估了其对NCI-H226非小细胞肺癌和非小细胞肺癌的细胞毒性。 A-498肾癌细胞系。在3-（5-羟甲基-2-呋喃基）衍生物（观察到的细胞毒性显著2，33，36和37）。其中，发现化合物2具有最有效的活性。化合物2的作用方式似乎与NCI标准数据库中列出的175种抗癌药不同，类似于YC-1。因此，我们建议化合物2 应进一步发展为治疗非小细胞肺癌和肾癌的新药候选药物。
• Ferrocenylmethyl-functionalized 5-membered heterocycles: Synthesis, solid-state structure and electrochemical investigations
  作者：Deeb Taher、Asma Ghazzy、Firas F. Awwadi、Wissam Helal、Khaled Al Khalyfeh、Marcus Korb、Alexander Hildebrandt、Eduard Kovalski、Heinrich Lang

  DOI：10.1016/j.poly.2018.06.038

  日期：2018.9

  It was found that for 3a, a somewhat higher Fc/Fc+ redox potential (E0′) is observed when compared with the more electron-rich systems 3b,c,d. The molecular electronic structures of the title compounds were additionally investigated by DFT calculations, revealing different degrees of HOMO–LUMO energy gaps within the series, due to a lowering of the LUMO energy, depending on the nature of the heterocyclic

  用两当量的ClC（O）R（2）（a，R = 2-cC4H3O; b，R = 2-cC4H3S; c，R = 2-cC4H3Se; d，R = 3-cC4H3S）生成相应的二茂铁基羧酸铁Fe（η5- CH2OC（O）R）2（3a–d），而FcCH2OLi反应（Fc = Fe（η5-C5H5）（η5-C5H4））用摩尔比为2：1的2,5-（ClC（O））2-cC4H2X（5）（a，X = O; b，X = S; c，X = Se）生成2,5-（FcCH2OC （O））2-cC4H2X（6a–c）。化合物3a–d和6a–c通过元素分析，NMR（1H和13C 1H}）和IR光谱进行了表征。通过单晶X射线结构分析确定固态的3a，b，d的分子结构。化合物3a在单斜空间群P21 / c中结晶，而3b，d在三斜空间群P-1中结晶。酯基和杂原子相对于彼此呈反排列。使用[NnBu4] [B（C6F5）
• Synthesis and in vitro anticancer activity of 6,7-methylenedioxy (or 5-hydroxy-6-methoxy)-2-(substituted selenophenyl)quinolin-4-one analogs
  作者：Chien-Ting Chen、Mei-Hua Hsu、Yung-Yi Cheng、Chin-Yu Liu、Li-Chen Chou、Li-Jiau Huang、Tian-Shung Wu、Xiaoming Yang、Kuo-Hsiung Lee、Sheng-Chu Kuo

  DOI：10.1016/j.ejmech.2011.10.017

  日期：2011.12

  6,7-Methylenedioxy (or 5-hydroxy-6-methoxy)-2-(substituted selenophenyl)quinolin-4-ones and their isosteric compounds were synthesized and evaluated for anticancer activity. Structure activity relationships (SAR) of these compounds were established. Among all tested compounds, 6,7-methylenedioxy-2-(5-methylselenophen-2-yl)quinolin-4-one (4d) was found to be the most promising anticancer agent. In screening against NCI's 60 human tumor cell line panel, 4d exhibited highly selective and potent inhibitory activity against MDA-MB-435 melanoma. Furthermore, the results of COMPARE analysis suggested that 4d is an antimitotic agent with a different mechanism of action from the conventional antimitotic agents, such as colchicine, vinca alkaloids and paclitaxel. Therefore, 4d was identified as a new lead compound that merits further optimization. (C) 2011 Elsevier Masson SAS. All rights reserved.
• WO2008/70176
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  公开号：——

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