N-{2-[2-(2-tert-butoxycarbonylaminoethoxy)ethoxy]ethyl}acrylamide | 361433-00-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-{2-[2-(2-tert-butoxycarbonylaminoethoxy)ethoxy]ethyl}acrylamide
• 英文别名: tert-butyl (2-(2-(2-acrylamidoethoxy)ethoxy)ethyl)-carbamate；tert-butyl N-[2-[2-[2-(prop-2-enoylamino)ethoxy]ethoxy]ethyl]carbamate
• CAS: 361433-00-3
• 化学式: C₁₄H₂₆N₂O₅
• 分子量: 302.371
• InChiKey: BOVVEVITRJYSBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  21
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  85.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-{2-[2-(2-tert-butoxycarbonylaminoethoxy)ethoxy]ethyl}acrylamide 在 盐酸 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 35.17h， 生成 3,5-bis({2-[2-(2-acrylamidoethoxy)ethoxy]ethyl}carbamoyl)-1-methylpyridin-1-ium iodide
  参考文献：
  名称：

  Synthesis of Pyridine Acrylates and Acrylamides and Their Corresponding Pyridinium Ions as Versatile Cross-Linkers for Tunable Hydrogels

  摘要：

  A small library of cross-linkers for hydrogels was synthesized. The cross-linkers consisted of 2,6- and 3,5-diacylpyridine or 2,4,6-triacylpyridine as the core unit, which were tethered via ethylene glycol, amino ethanol, and 1,n-diamine spacers to terminal acrylate or acrylamide moieties. Esterification and amide formation of the terminal acryl units were found to be dependent on the ratio of NH/O in the spacer, the constitution pattern of the pyridine ring, and the total number of acryl groups. Thus, esters generally gave higher yields than amides decreasing with increasing number of NH in the spacer and with increasing number of acryl units. In the case of 3,5-diacylpyridine derivatives, these trends were less prominent as compared to the 2,6-diacylpyridine series, indicating that steric hindrance and unfavorable hydrogen bonding interaction of the spacers might influence the observed reactivity differences. The 3,5-diacylpyridines were converted to the N-methylpyridinium salts and selected members of both neutral and cationic 3,5-diacylpyridinium derivatives were submitted to hydrogelations with synthetic polymer poly(1-glycidylpiperazine) via aza-Michael addition and thiolated natural hyaluronan via thio-Michael reaction, respectively. Rheological properties of the resulting hydrogels were studied, revealing that both spacer type as well as charge affected elastic moduli and degree of swelling.

  DOI：

  10.1055/s-0033-1338614
• 作为产物：
  描述：

  丙烯酰氯 、 2-(2-(2-氨基乙氧基)乙氧基)乙基氨基甲酸叔丁酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 N-{2-[2-(2-tert-butoxycarbonylaminoethoxy)ethoxy]ethyl}acrylamide
  参考文献：
  名称：

  Synthesis of Pyridine Acrylates and Acrylamides and Their Corresponding Pyridinium Ions as Versatile Cross-Linkers for Tunable Hydrogels

  摘要：

  A small library of cross-linkers for hydrogels was synthesized. The cross-linkers consisted of 2,6- and 3,5-diacylpyridine or 2,4,6-triacylpyridine as the core unit, which were tethered via ethylene glycol, amino ethanol, and 1,n-diamine spacers to terminal acrylate or acrylamide moieties. Esterification and amide formation of the terminal acryl units were found to be dependent on the ratio of NH/O in the spacer, the constitution pattern of the pyridine ring, and the total number of acryl groups. Thus, esters generally gave higher yields than amides decreasing with increasing number of NH in the spacer and with increasing number of acryl units. In the case of 3,5-diacylpyridine derivatives, these trends were less prominent as compared to the 2,6-diacylpyridine series, indicating that steric hindrance and unfavorable hydrogen bonding interaction of the spacers might influence the observed reactivity differences. The 3,5-diacylpyridines were converted to the N-methylpyridinium salts and selected members of both neutral and cationic 3,5-diacylpyridinium derivatives were submitted to hydrogelations with synthetic polymer poly(1-glycidylpiperazine) via aza-Michael addition and thiolated natural hyaluronan via thio-Michael reaction, respectively. Rheological properties of the resulting hydrogels were studied, revealing that both spacer type as well as charge affected elastic moduli and degree of swelling.

  DOI：

  10.1055/s-0033-1338614

文献信息

• Synthesis, characterization and biological evaluation of a new photoactive hydrogel against Gram-positive and Gram-negative bacteria
  作者：Cinzia Spagnul、John Greenman、Mark Wainwright、Zeeniya Kamil、Ross W. Boyle

  DOI：10.1039/c5tb02569a

  日期：——

  alternative to conventional antibiotics for the efficient inactivation of pathogenic microorganisms. We report the synthesis, characterization and antibacterial activity of a polyacrylamide-based hydrogel (7), with a new photoactive phenothiazinium compound (6) immobilized on it, to be used as a novel water-sterilizing device. The hydrogel was characterized by IR and scanning electron microscopy and incorporation

  2013年，世界卫生组织报告说8.84亿人缺乏清洁饮用水。光动力抗微生物化学疗法（PACT）是常规抗生素有效灭活病原微生物的一种非常有前途的替代方法。我们报告的合成，表征和抗菌活性的聚丙烯酰胺基水凝胶（7），与固定在其上的新的光敏吩噻嗪鎓化合物（6），将其用作新型的水消毒装置。通过IR和扫描电子显微镜表征水凝胶，并通过UV-可见光谱确认染料的掺入。使用重组生物发光革兰氏阳性金黄色葡萄球菌RN4220和革兰氏阴性大肠杆菌DH5α进行了抗菌测试，以评估水凝胶灭活溶液中细菌菌株的能力。水凝胶的特征在于无序的微孔结构，并且能够产生活性氧。在以14.5 mW cm-2的白光照射25分钟后，水凝胶能够灭活金黄色葡萄球菌和大肠杆菌的浮游细胞（分别杀死3.3 log和2.3 log）。接触表面不会影响杀灭率，而杀灭率则通过增加水凝胶的总量来增加（染料总量从0.5 mg cm-3到2.5 mg cm-3时，从0
• Discovery of a novel covalent CDK4/6 inhibitor based on palbociclib scaffold
  作者：Huifang Shan、Xinyu Ma、Guoyi Yan、Meng Luo、Xinxin Zhong、Suke Lan、Jie Yang、Yuanyuan Liu、Chunlan Pu、Yu Tong、Rui Li

  DOI：10.1016/j.ejmech.2021.113432

  日期：2021.7
• Targeting Cysteine Located Outside the Active Site: An Effective Strategy for Covalent ALKi Design
  作者：Guoyi Yan、Xinxin Zhong、Chunlan Pu、Lin Yue、Huifang Shan、Suke Lan、Meng Zhou、Xueyan Hou、Jie Yang、Deyu Li、Shilong Fan、Rui Li

  DOI：10.1021/acs.jmedchem.0c01707

  日期：2021.2.11
• P1/P1′ modified HIV protease inhibitors as tools in two new sensitive surface plasmon resonance biosensor screening assays
  作者：Mathias Alterman、Hans Sjöbom、Pär Säfsten、Per-Olof Markgren、U.Helena Danielson、Markku Hämäläinen、Stefan Löfås、Johan Hultén、Björn Classon、Bertil Samuelsson、Anders Hallberg

  DOI：10.1016/s0928-0987(01)00109-9

  日期：2001.5

  The commonly used HIV-1 protease assays rely on measurements of the effect of inhibitions on the hydrolysis rate of synthetic peptides. Recently an assay based on surface plasmon resonance (SPR) was introduced. We have taken advantage of the fact that the SPR signal is proportional to the mass of the analyte interacting with the immobilised molecule and developed two new improved efficient competition assay methods. Thus. high molecular weight binders were used as amplifiers of the surface plasmon resonance signal. Linkers were attached by a Heck reaction to the para-positions of the P1/P1' benzyloxy groups of a linear C-2-symmetric C-terminal duplicated inhibitor to enable (a) biotin labelling or (b) direct immobilisation of the inhibitor to the biosensor surface matrix. The interaction properties of a series of 17 structurally diverse inhibitors was assessed and compared to previously reported data. The most sensitive assay was obtained by immobilising the enzyme and amplifying the signal with an antibody, giving a detection range between 0.1 nM and 10 muM Immobilisation of the inhibitor resulted in a stable and durable surface but a narrower detection range (1-100 nM). The two competition assays are anticipated to be very suitable for fast screening of potential HIV inhibitors. (C) 2001 Elsevier Science B.V. All rights reserved.
• Synthesis of Pyridine Acrylates and Acrylamides and Their Corresponding Pyridinium Ions as Versatile Cross-Linkers for Tunable Hydrogels
  作者：Günter Tovar、Heike Boehm、Sabine Laschat、Markus Mateescu、Isabell Nuss、Alexander Southan、Hayley Messenger、Seraphine Wegner、Julia Kupka、Monika Bach

  DOI：10.1055/s-0033-1338614

  日期：——

  A small library of cross-linkers for hydrogels was synthesized. The cross-linkers consisted of 2,6- and 3,5-diacylpyridine or 2,4,6-triacylpyridine as the core unit, which were tethered via ethylene glycol, amino ethanol, and 1,n-diamine spacers to terminal acrylate or acrylamide moieties. Esterification and amide formation of the terminal acryl units were found to be dependent on the ratio of NH/O in the spacer, the constitution pattern of the pyridine ring, and the total number of acryl groups. Thus, esters generally gave higher yields than amides decreasing with increasing number of NH in the spacer and with increasing number of acryl units. In the case of 3,5-diacylpyridine derivatives, these trends were less prominent as compared to the 2,6-diacylpyridine series, indicating that steric hindrance and unfavorable hydrogen bonding interaction of the spacers might influence the observed reactivity differences. The 3,5-diacylpyridines were converted to the N-methylpyridinium salts and selected members of both neutral and cationic 3,5-diacylpyridinium derivatives were submitted to hydrogelations with synthetic polymer poly(1-glycidylpiperazine) via aza-Michael addition and thiolated natural hyaluronan via thio-Michael reaction, respectively. Rheological properties of the resulting hydrogels were studied, revealing that both spacer type as well as charge affected elastic moduli and degree of swelling.