4-((3-(3-((tert-butyldimethylsilyl)oxy)phenyl)propyl)amino)-isoindoline-1,3-dione | 212914-75-5

• 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: 4-((3-(3-((tert-butyldimethylsilyl)oxy)phenyl)propyl)amino)-isoindoline-1,3-dione
• 英文别名: 3-[3-[Tert-butyl(dimethyl)silyl]oxyphenyl]propanal；3-[3-[tert-butyl(dimethyl)silyl]oxyphenyl]propanal
• CAS: 212914-75-5
• 化学式: C₁₅H₂₄O₂Si
• 分子量: 264.44
• InChiKey: UPRBHBVJVOQGJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-((3-(3-((tert-butyldimethylsilyl)oxy)phenyl)propyl)amino)-isoindoline-1,3-dione 在 aluminum oxide 、 甲基锂 、 lithium bromide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 7.0h， 生成 Carbamic acid (6Z,11Z)-(1S,2R,3R,4S,8S,9S,10S)-3,9-bis-(tert-butyl-dimethyl-silanyloxy)-14-[3-(tert-butyl-dimethyl-silanyloxy)-phenyl]-2,4,8,10-tetramethyl-1-((Z)-(S)-1-methyl-penta-2,4-dienyl)-tetradeca-6,11-dienyl ester
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of Analogues of (+)-14-Normethyldiscodermolide

  摘要：

  The design, syntheses, and biological evaluation of nine totally synthetic analogues of the microtubule-stabilizing agent (divided by)-14-normethyldiscodermolide (2) are reported. Simplification at the C(21)-C(24) terminal diene and at the C(1)-C(5) lactone moieties reveals significant structure-activity relationships.

  DOI：

  10.1021/ol0476873
• 作为产物：
  描述：

  硅烷,[3-(溴甲基)苯氧基](1,1-二甲基乙基)二甲基- 在 臭氧 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 4.67h， 生成 4-((3-(3-((tert-butyldimethylsilyl)oxy)phenyl)propyl)amino)-isoindoline-1,3-dione
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of Analogues of (+)-14-Normethyldiscodermolide

  摘要：

  The design, syntheses, and biological evaluation of nine totally synthetic analogues of the microtubule-stabilizing agent (divided by)-14-normethyldiscodermolide (2) are reported. Simplification at the C(21)-C(24) terminal diene and at the C(1)-C(5) lactone moieties reveals significant structure-activity relationships.

  DOI：

  10.1021/ol0476873

文献信息

• Small Molecule Inhibitors of the BfrB–Bfd Interaction Decrease <i>Pseudomonas aeruginosa</i> Fitness and Potentiate Fluoroquinolone Activity
  作者：Achala N. D. Punchi Hewage、Huili Yao、Baskar Nammalwar、Krishna Kumar Gnanasekaran、Scott Lovell、Richard A. Bunce、Kate Eshelman、Sahishna M. Phaniraj、Molly M. Lee、Blake R. Peterson、Kevin P. Battaile、Allen B. Reitz、Mario Rivera

  DOI：10.1021/jacs.9b00394

  日期：2019.5.22

  inhibitors of the BfrB–Bfd protein–protein interaction. The process was initiated by screening a fragment library and followed by obtaining the structure of a fragment hit bound to BfrB. The structural insights were used to develop a series of 4-(benzylamino)- and 4-((3-phenylpropyl)amino)-isoindoline-1,3-dione analogs that selectively bind BfrB at the Bfd binding site. Challenging P. aeruginosa cells with

  储铁蛋白细菌铁蛋白 (BfrB) 是细菌铁稳态的核心。从 BfrB 中动员铁，这需要通过同源铁氧还蛋白 (Bfd) 结合，对于调节铜绿假单胞菌中的细胞溶质铁水平至关重要。本文描述了 BfrB-Bfd 蛋白质-蛋白质相互作用的小分子抑制剂的结构引导开发。该过程通过筛选片段文库开始，然后获得与 BfrB 结合的片段命中结构。结构见解用于开发一系列 4-(苄基氨基)-和 4-((3-苯基丙基)氨基)-isoindoline-1,3-dione 类似物，它们在 Bfd 结合位点选择性结合 BfrB。用 4 取代异二氢吲哚类似物挑战铜绿假单胞菌细胞显示出剂量依赖性生长表型。进一步的研究确定，这些类似物引发了一种pyoverdin 过度生产表型，这与 BfrB-Bfd 相互作用的阻断和随之而来的铁在 BfrB 中的不可逆积累一致，伴随着细胞质中铁的消耗。通过在天然 PAGE 凝胶上分离的铜绿假单胞菌细胞裂解物中的
• [EN] SMALL MOLECULE INHIBITORS OF THE BFRB:BFD INTERACTION<br/>[FR] INHIBITEURS À PETITES MOLÉCULES DE L'INTERACTION BFRB-BFD
  申请人：UNIV KANSAS

  公开号：WO2020117832A1

  公开（公告）日：2020-06-11

  The present technology provides compounds of Formula I and related methods for treating a bacterial infection as well as methods for inhibiting interaction of a bacterioferritin and a bacterioferritin-associated ferredoxin.

  目前的技术提供了Formula I化合物以及相关方法，用于治疗细菌感染，以及抑制细菌铁蛋白和细菌铁蛋白相关的叶绿素蛋白之间的相互作用的方法。
• Au-Catalyzed Asymmetric Polyene Cyclization and Its Application in the Total Synthesis of (+)-2-Ketoferruginol, (+)-Fleuryinol B, (+)-Salviol, and (−)-Erythroxylisin A
  作者：Tian-Lu Zheng、Chen-Yu Huo、Wen Bao、Xue-Tao Xu、Wei-Hao Dai、Fu Cheng、Dong-Sen Duan、Le-Le Yang、Xiao-Ming Zhang、Dao-Yong Zhu、Shao-Hua Wang

  DOI：10.1021/acs.orglett.3c02417

  日期：2023.10.20

  shift/polyene cyclization cascade has been achieved with good enantioselectivities under the catalysis of the chiral Au(I) reagent. The synthetic utility of this method has been showcased by the catalytic asymmetric total syntheses of (+)-2-ketoferruginol, (+)-fleuryinol B, and (+)-salviol. Notably, the first enantioselective total synthesis of (−)-erythroxylisin A has also been realized in 15 steps.

  在手性 Au(I) 试剂的催化下，实现了催化不对称 1,3-酰氧基转移/多烯环化级联，具有良好的对映选择性。(+)-2-ketoferruginol、(+)-fleuryinol B 和 (+)-salviol 的催化不对称全合成展示了该方法的合成实用性。值得注意的是，(−)-erythroxylisin A 的首次对映选择性全合成也通过 15 个步骤实现。
• Design, synthesis and cytotoxicity of 7-deoxy aryl discodermolide analogues
  作者：Mark A Burlingame、Simon J Shaw、Kurt F Sundermann、Dan Zhang、Joseph Petryka、Esteban Mendoza、Fenghua Liu、David C Myles、Matthew J LaMarche、Tomoyasu Hirose、B Scott Freeze、Amos B Smith

  DOI：10.1016/j.bmcl.2004.01.102

  日期：2004.5

  A series of 7-deoxy discodermolide analogues in which the lactone fragment 'C' was replaced by aryl substituents were designed, synthesized, and evaluated for cytotoxicity. (C) 2004 Elsevier Ltd. All rights reserved.
• Design, Synthesis, and Evaluation of Analogues of (+)-14-Normethyldiscodermolide
  作者：Amos B. Smith、B. Scott Freeze、Matthew J. LaMarche、Tomoyasu Hirose、Ignacio Brouard、Ming Xian、Kurt F. Sundermann、Simon J. Shaw、Mark A. Burlingame、Susan Band Horwitz、David C. Myles

  DOI：10.1021/ol0476873

  日期：2005.1.1

  The design, syntheses, and biological evaluation of nine totally synthetic analogues of the microtubule-stabilizing agent (divided by)-14-normethyldiscodermolide (2) are reported. Simplification at the C(21)-C(24) terminal diene and at the C(1)-C(5) lactone moieties reveals significant structure-activity relationships.