2-(2-thienyl)perimidine | 62460-65-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类 - 二氮杂萘
• 英文名称: 2-(2-thienyl)perimidine
• 英文别名: 2-(thiophen-2-yl)-1H-perimidine；1H-2-(2-thienyl)perimidine；2-thiophen-2-yl-1H-perimidine
• CAS: 62460-65-5
• 化学式: C₁₅H₁₀N₂S
• 分子量: 250.324
• InChiKey: SRNKJEHQROCWRO-UHFFFAOYSA-N

物化性质

• 熔点：
  166-168 °C(Solv: cyclohexane (110-82-7))
• 沸点：
  483.7±27.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-thienyl)perimidine 在 溶剂黄146 、 sodium hydroxide 、 sodium nitrite 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 、
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel perimidine o-quinone derivatives as non-intercalative topoisomerase II catalytic inhibitors

  摘要：

  For the development of novel anticancer agents, we designed and synthesized a total of 37 perimidine o-quinone derivatives containing the o-quinone group at the A or B ring and different substituents (alkyl groups, aryl groups or heterocycles) at the C ring of the compounds. The structure-activity relationships (SARs) were established based on the cytotoxicity data of compounds from the HL-60, Huh7, Hct116, and Hela cell lines. The cytotoxicity results showed that most compounds exhibited potent cytotoxicity. In particular, compound b-12 showed the best anti-proliferative activity (IC50 <= 1 mu M) against four cancer cell lines and strong potency against the HL-60/MX2 (0.47 mu M) cell line, which is resistant to Topo II poisons. Further studies showed that b-12 exhibited potent Topo II alpha inhibitory activity (IC50 = 7.54 mu M) compared with Topo I, which acted as a class of non-intercalative Topo IIa catalytic inhibitor by inhibiting the ATP binding site of Topo II. Cell apoptosis and cell cycle assays confirmed that b-12 could induce the apoptosis of Huh7 cells in a dose-dependent manner.

  DOI：

  10.1016/j.bioorg.2019.103131
• 作为产物：
  描述：

  2-(thiophen-2-yl)-2,3-dihydro-1H-perimidine 在 sodium disulfite 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 以98%的产率得到2-(2-thienyl)perimidine
  参考文献：
  名称：

  二烯的杂环类似物

  摘要：

  DOI：

  10.1007/bf00475399

文献信息

• A Panchromatic Cyclometalated Iridium Dye Based on 2-Thienyl-Perimidine
  作者：Paulina Kalle、Marina A. Kiseleva、Sergei V. Tatarin、Daniil E. Smirnov、Alexander Y. Zakharov、Viktor V. Emets、Andrei V. Churakov、Stanislav I. Bezzubov

  DOI：10.3390/molecules27103201

  日期：——

  Though 2-arylperimidines have never been used in iridium(III) chemistry, the present study on structural, electronic and optical properties of N-unsubstituted and N-methylated 2-(2-thienyl)perimidines, supported by DFT/TDDFT calculations, has shown that these ligands are promising candidates for construction of light-harvesting iridium(III) complexes. In contrast to N-H perimidine, the N-methylated

  虽然 2-芳基哌啶从未用于铱 (III) 化学，但目前在DFT/TDDFT 计算的支持下，对N-未取代和N-甲基化 2-(2-噻吩基) 嘧啶的结构、电子和光学性质的研究已经表明这些配体是构建捕光铱（III）配合物的有希望的候选者。与N -H perimidine 相比，N-甲基化配体产生预期的环金属化 μ-氯桥接铱 (III) 二聚体，其很容易转化为具有 4,4'-二羧基-2,2'-联吡啶的阳离子杂配络合物. 得到的铱 (III) 染料表现出高达 1000 nm 的全色吸收，并在染料敏化太阳能电池中进行了测试。
• Application of Bertagnini's Salts in a Mechanochemical Approach Toward Aza‐Heterocycles and Reductive Aminations via Imine Formation
  作者：Sourav Behera、Shyamal Kanti Bera、Francesco Basoccu、Federico Cuccu、Pietro Caboni、Lidia De Luca、Andrea Porcheddu

  DOI：10.1002/adsc.202301407

  日期：——

  with solid reagents. We have showcased the practicality of Bertagnini's salts, also called aldehyde-bisulfite adducts, which are crystalline, simplifying preparation and storage. These salts are stable substitutes for liquid aldehydes and ketones that have been effectively employed in reductive amination, synthesizing aza-heterocycles and hydrazones within mechanochemistry. The technique's effectiveness

  我们的研究表明，使用固体试剂进行机械化学活化更有效。我们展示了贝尔塔尼尼盐（也称为醛-亚硫酸氢盐加合物）的实用性，它们是结晶，简化了制备和储存。这些盐是液体醛和酮的稳定替代品，可有效用于机械化学中的还原胺化、氮杂杂环和腙的合成。该技术的有效性拓宽了底物范围，简化了纯化，减少了反应时间，并提供了良好的产物收率。此外，亚硫酸氢盐加合物的热稳定性已通过 TGA（热重分析）分析得到证实。
• An Improved One-Pot Method for the Preparation of 2-Substituted 1H-Perimidines
  作者：André Maquestiau、Laurence Berte、Annie Mayence、Jean-Jacques Vanden Eynde

  DOI：10.1080/00397919108055450

  日期：1991.11

  2-substituted H-1-perimidines are readily prepared, in high yields, by refluxing a mixture of sodium pyrosulfite, an aldehyde, and 1,8-diaminonaphthalene in aqueous ethanol or N,N-dimethylformamide. The method is of wide applicability except from araldehydes bearing a strong electron-withdrawing group (-CN, -NO2).
• STARSHIKOV N. M.; POZHARSKIJ A., XIMIYA GETEROTSIKL. SOEDIN., 1980, HO 1, 96-100
  作者：STARSHIKOV N. M.、 POZHARSKIJ A.

  DOI：——

  日期：——
• POZHARSKIJ A. F.; STARSHIKOV N. M.; POZHARSKIJ F. T.; MANDRYKIN YU. I., XIMIYA GETEROTSIKL. SOEDIN., 1977, HO 7, 980-985
  作者：POZHARSKIJ A. F.、 STARSHIKOV N. M.、 POZHARSKIJ F. T.、 MANDRYKIN YU. I.

  DOI：——

  日期：——