1-{4-[2-(pyrrolidin-1-yl)ethoxy]phenyl}ethan-1-one | 26815-00-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-{4-[2-(pyrrolidin-1-yl)ethoxy]phenyl}ethan-1-one
• 英文别名: 4'-[2-(pyrrolidin-1-yl)ethoxy]acetophenone；1-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-ethanone；4'-[2-(1-pyrrolidinyl)ethoxy]-acetophenone；1-[4-(2-Pyrrolidin-1-ylethoxy)phenyl]ethanone
• CAS: 26815-00-9
• 化学式: C₁₄H₁₉NO₂
• mdl: MFCD11171172
• 分子量: 233.31
• InChiKey: CIOUJKSZZRBSJM-UHFFFAOYSA-N

物化性质

• 沸点：
  369.1±22.0 °C(Predicted)
• 密度：
  1.073±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-{4-[2-(pyrrolidin-1-yl)ethoxy]phenyl}ethan-1-one 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 氯苯 为溶剂， 生成 [2-Methoxy-4-[[2-[4-(2-pyrrolidin-1-ylethoxy)phenyl]indol-1-yl]methyl]phenyl]methanol
  参考文献：
  名称：

  1,2-disubstituted indole, azaindole and benzimidazole derivatives possessing amine moiety: a novel series of thrombin inhibitors

  摘要：

  A novel series of 1,2-disubstituted indole, azaindole and benzimidazole derivatives possessing an amine moiety was identified as thrombin inhibitors. An indole with basic diamine moieties (12a) was the most potent thrombin inhibitor in the series with K-ass = 197 x 10(6) L/mol. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00454-6
• 作为产物：
  描述：

  对羟基苯乙酮 在 potassium carbonate 、 溶剂黄146 作用下， 以 乙醇 、 丙酮 为溶剂， 生成 1-{4-[2-(pyrrolidin-1-yl)ethoxy]phenyl}ethan-1-one
  参考文献：
  名称：

  新型吡唑-查耳酮杂化物：抗乳腺癌的合成和计算见解

  摘要：

  死于乳腺癌的女性比死于其他恶性肿瘤的女性还要多。传统激素疗法的耐药性和毒性迫切需要有效治疗乳腺癌的潜在分子。通过使用杂交方法设计了与吡咯烷环连接的新型联苯取代的吡唑查耳酮。通过 NRU 测定针对 MCF-7 和 MDA-MB-231 细胞评估杂交体。其中，与阳性对照雷洛昔芬相比，8 k、8 d、8 m、8 h 和 8 f 对 MCF-7 细胞显示出显着有效的 IC 50值：分别为 0.17、5.48、8.13、20.51 和 23.61 μM)和他莫昔芬。此外，最活跃的化合物8 k [3-(3-(4-氟苯基)-1-苯基-1H-吡唑-4-基)-1-(2-(2-(吡咯烷-1-基)-乙氧基) -苯基)-查尔酮]通过细胞凋亡诱导细胞死亡，细胞周期停滞在 G2/M 期，并在蛋白质印迹研究中证明 ER-α 蛋白减少。 8 k和8 d的对接研究确定了与 SERM 结合所需的与雌激素受体-α 的充分相互作

  DOI：

  10.1002/cbdv.202400015

文献信息

• Substituted acrylophenones and related mannich bases as possible spermicides and inhibitors of HIV envelope glycoprotein–CD4 interaction
  作者：Niharika Kumaria、Anil Kumar Dwivedi、Jagdamba Prasad Maikhuri、Gopal Gupta、Saman Habib、Janak Dulari Dhar、Satyawan Singh

  DOI：10.1016/s0223-5234(01)01292-2

  日期：2002.11

  subjected to the Mannich reaction to yield compounds that would incorporate both alpha,beta-unsaturated keto groups and a substituted aminomethyl function with or without another olefinic moiety at position 4. The spermicidal activity of the prepared compounds was evaluated. Several compounds 2d, 4a and 4e were found to possess spermicidal activity at 0.005% concentration, while compounds 2a, 2c, 2f, 3a and

  制备了几种适当取代的4-（二烷基氨基-烷基）-取代的苯乙烯基-烷基酮或苯乙酮，并进行曼尼希反应，得到的化合物将同时包含α，β-不饱和酮基和具有或不具有另一个的取代的氨基甲基官能团在4位的烯基部分。评估了所制备化合物的杀精活性。发现几种化合物2d，4a和4e在0.005％浓度下具有杀精活性，而化合物2a，2c，2f，3a和4b在0.01％浓度下具有活性。化合物2a，2c，3a，4a和4e也抑制重组HIV Env和CD4之间的相互作用。在这些化合物中，发现化合物2c最具活性。
• Design and synthesis of 1,3-biarylsulfanyl derivatives as new anti-breast cancer agents
  作者：Atul Kumar、Vishwa Deepak Tripathi、Promod Kumar、Lalit Prakash Gupta、Akanksha、Ritu Trivedi、Hemant Bid、V.L. Nayak、Jawed A. Siddiqui、Bandana Chakravarti、Ruchi Saxena、Anila Dwivedi、M.I. Siddiquee、U. Siddiqui、Rituraj Konwar、Naibedya Chattopadhyay

  DOI：10.1016/j.bmc.2011.07.056

  日期：2011.9

  A new series of 1,3-biarylsulfanyl derivatives (homodibenzyl core motif) have been designed and synthesized as new estrogen receptor ligands by chopping benzothiophene core of raloxifene to engender secoraloxifene scaffold. All the synthesized compounds were screened for anti-proliferative, anti-osteoporotic, and anti-implantation activity. Compounds (35, 36) having basic amino anti-estrogenic side chain were exhibiting potential anti-proliferative activity in MCF-7, MDA-MB-231 and ishikawa cell lines. Some of the synthesized compounds having homodibenzyl motif (5, 8, 10) have shown moderate anti-osteoporotic activity. (C) 2011 Elsevier Ltd. All rights reserved.
• Discovery of 3-phenylquinolinylchalcone derivatives as potent and selective anticancer agents against breast cancers
  作者：Chih-Hua Tseng、Cherng-Chyi Tzeng、Chih-Yao Hsu、Chih-Mei Cheng、Chia-Ning Yang、Yeh-Long Chen

  DOI：10.1016/j.ejmech.2015.04.054

  日期：2015.6

  A number of 3-phenylquinolinylchalcone derivatives were synthesized and evaluated in vitro for their antiproliferative activities against three breast cancer cell lines (MCF-7, MDA-MB-231, and SKBR-3), and a non-cancer normal epithelial cell line (H184B5F5/M10). Among them, (E)-3-[3-(4-methoxyphenyl)quinolin-2-yl]-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (7) was active against the growth of MCF-7, MDA-MB-231, and SKBR-3 with IC50 values of 1.05, 0.75, and 0.78 mu M respectively without significant cytotoxicity to the normal H184B5F5/M10 cell line and therefore, was selected as a new lead for further mechanism studies. Results indicated that compound 7 inhibited the polymerization of tubulins, induced G2/M cell cycle arrest via modulation of the cyclin B1, cdk1 and CDC25. Compound 7 ultimately induced cell apoptosis by the increase of apoptotic protein Bax and the decrease of anti-apoptotic protein Bcl-2. In addition, PARP was cleaved while caspase-3 and -8 activities were induced after the treatment of compound 7 for 24 h in a concentration-dependent manner. Thus, compound 7 induces cell cycle arrest at G2/M phase via cleavage of PARP, induces caspase-3 and -8 activities and consequently to cause the cell death. Further study on the structure optimization of 7 is ongoing. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Design and synthesis of ligustrazine derivatives as potential anti-Alzheimer’s agents
  作者：Xu-fei Chen、Shan-shan Li、Yu-jun Bai、Ze-feng Zhao、Ya-jun Bai、Gu Gong、Xi-rui He、Xiao-hui Zheng

  DOI：10.1080/14786419.2023.2241155

  日期：——
• ANTITHROMBOTIC AGENTS
  申请人：ELI LILLY AND COMPANY

  公开号：EP1011666A1

  公开（公告）日：2000-06-28