3-methylpentane-1,5-diyl bis(4-methylbenzenesulfonate) | 148054-23-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-methylpentane-1,5-diyl bis(4-methylbenzenesulfonate)
• 英文别名: [3-methyl-5-(4-methylphenyl)sulfonyloxypentyl] 4-methylbenzenesulfonate
• CAS: 148054-23-3
• 化学式: C₂₀H₂₆O₆S₂
• 分子量: 426.555
• InChiKey: YFRSEKYEPSVPCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-methylpentane-1,5-diyl bis(4-methylbenzenesulfonate) 在 盐酸羟胺 、 sodium hydride 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 26.0h， 生成 N-Hydroxy-4-[3-methyl-5-(2-oxo-3-pyridin-4-yl-imidazolidin-1-yl)-pentyloxy]-benzamidine
  参考文献：
  名称：

  Design, Synthesis, and Antipicornavirus Activity of 1-[5-(4-Arylphenoxy)alkyl]-3-pyridin-4-ylimidazolidin-2-one Derivatives

  摘要：

  A series of pyridylimidazolidinone derivatives was synthesized and tested in vitro against enterovirus 71 (EV71). On the basis of compound 33 (DBPR103), introduction of a methyl group at the 2- or 3-position of the linker between the imidazolidinone and the biphenyl resulted in markedly improved antiviral activity toward EV71 with IC50 values of 5.0 nM (24b) and 9.3 nM (14a), respectively. Increasing the branched chain to propyl resulted in a progressive decrease in activity, while inserting different heteroatoms entirely rendered the compound only weakly active. The introduction of a bulky group (cyclohexyl, phenyl, or benzyl) led to loss of activity against EV71. The 4-chlorophenyl moiety in 14a was replaced with bioisosteric groups such as oxadiazole (28a-d) or tetrazole (32a,b), dramatically improving anti-EV71 activity and selectivity indices. Compounds 14a, 24b, 28b, 28d, and 32a exhibited a strong activity against lethal EV71, and no apparent cellular toxicity was observed. Three of the more potent imidazolidinone compounds, 14a, 28b, and 32b, were subjected to a large group of picornaviruses to determine their spectrum of antiviral activity.

  DOI：

  10.1021/jm050033v
• 作为产物：
  描述：

  戊烯二酸二甲酯 在 吡啶 、 copper(l) iodide 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 26.0h， 生成 3-methylpentane-1,5-diyl bis(4-methylbenzenesulfonate)
  参考文献：
  名称：

  Design, Synthesis, and Antipicornavirus Activity of 1-[5-(4-Arylphenoxy)alkyl]-3-pyridin-4-ylimidazolidin-2-one Derivatives

  摘要：

  A series of pyridylimidazolidinone derivatives was synthesized and tested in vitro against enterovirus 71 (EV71). On the basis of compound 33 (DBPR103), introduction of a methyl group at the 2- or 3-position of the linker between the imidazolidinone and the biphenyl resulted in markedly improved antiviral activity toward EV71 with IC50 values of 5.0 nM (24b) and 9.3 nM (14a), respectively. Increasing the branched chain to propyl resulted in a progressive decrease in activity, while inserting different heteroatoms entirely rendered the compound only weakly active. The introduction of a bulky group (cyclohexyl, phenyl, or benzyl) led to loss of activity against EV71. The 4-chlorophenyl moiety in 14a was replaced with bioisosteric groups such as oxadiazole (28a-d) or tetrazole (32a,b), dramatically improving anti-EV71 activity and selectivity indices. Compounds 14a, 24b, 28b, 28d, and 32a exhibited a strong activity against lethal EV71, and no apparent cellular toxicity was observed. Three of the more potent imidazolidinone compounds, 14a, 28b, and 32b, were subjected to a large group of picornaviruses to determine their spectrum of antiviral activity.

  DOI：

  10.1021/jm050033v

文献信息

• 3-(5-HYDROXY-1-OXOISOINDOLIN-2-YL)PIPERIDINE-2,6-DIONE DERIVATIVES AND USES THEREOF
  申请人：Novartis AG

  公开号：US20200017461A1

  公开（公告）日：2020-01-16

  The present disclosure provides a compound of Formula (I′): or a pharmaceutically acceptable salt, hydrate, solvate, prodrug, stereoisomer, or tautomer thereof, wherein R x , X 1 , X 2 , and R 1 are as defined herein, and methods of making and using same.

  本公开提供了化合物Formula (I′)的一种： 或其药用可接受的盐、水合物、溶剂合物、前药、立体异构体或互变异构体，其中R x 、X 1 、X 2 和R 1 如本文所定义，并提供了制备和使用该化合物的方法。
• ANTI-ENTEROVIRUS 71 THIADIAZOLIDINE DERIVATIVE
  申请人：JIANGSU KANION PHARMACEUTICAL CO. LTD

  公开号：US20170066732A1

  公开（公告）日：2017-03-09

  Disclosed is a novel anti-enterovirus 71 (EV71) 1,2,5-thiadiazolidine-1,1-dioxide derivative or a pharmaceutically acceptable salt thereof; and specifically, a compound represented by formula (II) or a pharmaceutically acceptable salt thereof.

  揭示了一种新型抗肠道病毒71（EV71）1,2,5-噻二唑啉-1,1-二氧化物衍生物或其药用盐；具体而言，是由式（II）表示的化合物或其药用盐。
• Novel potential pyrazolopyrimidine based translocator protein ligands for the evaluation of neuroinflammation with PET
  作者：Young-Do Kwon、Shinwoo Kang、Hyunjun Park、Il-koo Cheong、Keun-A Chang、Sang-Yoon Lee、Jae Ho Jung、Byung Chul Lee、Seok Tae Lim、Hee-Kwon Kim

  DOI：10.1016/j.ejmech.2018.09.069

  日期：2018.11

  in vitro affinity study suggests that 2-(5,7-diethyl-2-(4-(3-fluoro-2-methylpropoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-N,N-diethylacetamide (14a), which exhibited high nano-molar affinity for TSPO and proper lipophilicity, was suitable for in vivo brain studies. Thus, radiosynthesis from tosylate precursor 13a using fluorine-18 was performed, and [18F]14a was obtained in a 31% radiochemical yield (decay-corrected)

  转运蛋白（TSPO）是一个有趣的生物学靶标，因为TSPO的过表达与神经元损伤或神经发炎引起的小胶质细胞活化有关，而这些活化的小胶质细胞与几种中枢神经系统疾病有关。在此，合成了基于2-苯基吡唑并[1,5 - a ]嘧啶-3-基乙酰胺支架的新型氟化配体（14a–c和16a–c），并对每种新型配体进行了体外表征阐明结构活动关系。所有新合成的配体均显示出对TSPO的纳摩尔摩尔亲和力。特别是体外亲和力研究表明，2-（5,7-二乙基-2-（4-（3-氟-2-甲基丙氧基）苯基）吡唑并[1,5 - a ]嘧啶-3-基）-N，N-二乙基乙酰胺（对TSPO表现出高纳摩尔摩尔亲和力和适当的亲脂性的14a）适用于体内脑研究。因此，使用氟-18从甲苯磺酸酯前体13a进行了放射性合成，以31％的放射化学收率（校正了衰变）获得了[ 18 F] 14a。使用[ 18 F] 14a在脂多糖（LPS）诱导的神经炎症大鼠模型中
• [EN] ANTI-ENTEROVIRUS 71 THIADIAZOLIDINE DERIVATIVE<br/>[FR] DÉRIVÉ DE THIADIAZOLIDINE ANTI-ENTÉROVIRUS 71<br/>[ZH] 抗肠病毒71噻二唑烷衍生物
  申请人：MEDSHINE DISCOVERY INC

  公开号：WO2015165340A1

  公开（公告）日：2015-11-05

  本发明公开了新的抗肠道病毒71型（EV71）1,2,5-噻二唑烷-1,1-二氧化物衍生物或其药学上可接受的盐，具体公开了式（Ⅱ）所示化合物或其药学上可接受的盐。
• Synthesis and antipicornavirus activity of (R)- and (S)-1-[5-(4′-chlorobiphenyl-4-yloxy)-3-methylpentyl]-3-pyridin-4-yl-imidazolidin-2-one
  作者：Jyh-Haur Chern、Chih-Shiang Chang、Chia-Liang Tai、Yen-Chun Lee、Chung-Chi Lee、Iou-Jiun Kang、Ching-Yin Lee、Shin-Ru Shih

  DOI：10.1016/j.bmcl.2005.06.069

  日期：2005.10

  The new pyridyl imidazolidinone derivative, 1-[5-(4'-chlorobiphenyl-4-yloxy)-3-methylpentyl]-3-pyridin-4-yl-imidazolidin-2-one (+/-)-1a, was synthesized and found to have an excellent antiviral activity against EV71 (IC50 = 0.009 mu M). Therefore, both the enantiomers, (S)-(+)-1a and (R)-(-)-1a, have been prepared starting from readily available monomethyl (R)-3-methylglutarate (7) as a useful chiral building block and their antiviral activity was evaluated in a plaque reduction assay. Interestingly, we observed that the enantiomer (S)-(+)-1a was 10-fold more active against enterovirus71 (EV71) (IC50 = 0.003 mu M) than the corresponding enantiomer (R)-(-)-1a (IC50 = 0.033 mu M). Similar results were found against all five strains (1743, 2086, 2231, 4643, and BrCr) of EV71 tested. This demonstrated that the absolute configuration of the chiral carbon atom at the 3-position of the alkyl linker considerably influenced the anti-EV71 activity of these pyridyl imidazolidinones. (c) 2005 Elsevier Ltd. All rights reserved.