2-aminoethyl 2-(4-isobutylphenyl)propanoate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2-aminoethyl 2-(4-isobutylphenyl)propanoate
• 英文别名: 2-Aminoethyl 2-[4-(2-methylpropyl)phenyl]propanoate
• 化学式: C₁₅H₂₃NO₂
• 分子量: 249.353
• InChiKey: QNRXLXCCKXOSST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-aminoethyl 2-(4-isobutylphenyl)propanoate 在 1-辛硫醇 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 37.0h， 生成
  参考文献：
  名称：

  10.1007/s11095-024-03747-6

  摘要：

  Abstract Objective The development of an efficient, multifunctional drug delivery system overcoming different obstacles generally associated with drug formulations, including the poor accumulation of the active principle in the target site and its sustained release for prolonged time. Methods Our study proposes the development of a fluorinated poly(amidoamine) (PAMAM) carrier prodrug combining drug release boosted in alkaline environments with a possible implementation in 19F MRI applications. In particular, we functionalized the terminal primary amines of PAMAM G2 and G4 through an ad hoc designed fluorinated ibuprofen-arginine Michael acceptor to obtain multifunctional ibuprofen-PAMAM-Arg conjugates. Results These carriers demonstrated pH-dependent and sustained ibuprofen release for more than 5 days. This advantage was observed in both weak alkaline and physiological buffer solutions, allowing to overcome the limits associated to the burst release from similar fluorinated Arg-PAMAM dendrimers with ibuprofen physically encapsulated. Conclusion These findings, coupled to the high biocompatibility of the system, suggest a potential synergistic biomedical application of our conjugates, serving as vehicles for drug delivery and as 19F magnetic resonance imaging contrast agents.

  DOI：

  10.1007/s11095-024-03747-6
• 作为产物：
  描述：

  2-(4-isobutylphenyl)propionic acid 2-tert-butoxycarbonylaminoethyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 2-aminoethyl 2-(4-isobutylphenyl)propanoate
  参考文献：
  名称：

  荧光标记的环氧合酶-2抑制剂对癌症中环氧合酶-2过表达的成像：合成和生物学研究

  摘要：

  通过将抗炎药布洛芬，（S）-萘普生和塞来昔布与7-硝基苯并呋喃山（NBD）荧光团连接，合成了一组特定于环氧合酶2（COX-2）的荧光癌生物标记。体外COX-1 / COX-2抑制的研究表明，所有这些荧光缀合物的是COX-2抑制剂（IC 50范围：0.19-23.0μ中号）与可感知的COX-2选择性指数（SI≥4.3-444）。在这项研究中，塞来昔布-NBD共轭N-（2-（（7-硝基苯并[ c ] [1,2,5]恶二唑-4-基）氨基）乙基）-4-（5-（对甲苯基）- 3-（三氟甲基）-1 H-吡唑-1-基）苯磺酰胺（14），其显示的最高COX-2抑制的效力和选择性（COX-2的IC 50 = 0.19μ中号;使用COX-SI = 443.6），被认定为即将发生的COX-2特异性的生物标记用于癌症的荧光成像2表达人类结肠癌细胞系（HCA-7）。

  DOI：

  10.1002/cmdc.201300355

文献信息

• Hybrid fluorescent conjugates of COX-2 inhibitors: Search for a COX-2 isozyme imaging cancer biomarker
  作者：Atul Bhardwaj、Jatinder Kaur、Sai Kiran Sharma、Zhangjian Huang、Frank Wuest、Edward E. Knaus

  DOI：10.1016/j.bmcl.2012.10.131

  日期：2013.1

  The observation that the cyclooxygenase-2 (COX-2) isozyme is over-expressed in multiple types of cancer, relative to that in adjacent non-cancerous tissue, prompted this investigation to prepare a group of hybrid fluorescent conjugates wherein the COX inhibitors ibuprofen, (S)-naproxen, acetyl salicylic acid, a chlororofecoxib analog and celecoxib were coupled via a linker group to an acridone, dansyl or rhodamine B fluorophore. Within this group of compounds, the ibuprofen-acridone conjugate (10) showed potent and selective COX-2 inhibition (COX-2 IC50 = 0.67 mu M; SI = 110.6), but its fluorescence emission (lambda(em) = 417, 440 nm) was not suitable for fluorescent imaging of cancer cells that over-express the COX-2 isozyme. In comparison, the celecoxib-dansyl conjugate (25) showed a slightly lower COX-2 potency and selectivity (COX-2 IC50 = 1.1 mu M; SI > 90) than the conjugate 10, and it possesses a better fluorescence emission (lambda(em) = 500 nm). Ultimately, a celecoxib-rhodamine B conjugate (28) that exhibited moderate COX-2 potency and selectivity (COX-2 IC50 = 3.9 mu M; SI > 25) having the best fluorescence emission (lambda(em) = 580 nm) emerged as the most promising biomarker for fluorescence imaging using a colon cancer cell line that over-expresses the COX-2 isozyme. (C) 2012 Elsevier Ltd. All rights reserved.
• BORA, G.;BEU, L.;RUSSU, J.;BREAZU, D.;FARCASANU, I.;FABIAN, A.;TODOR, S., REV. CHIM., RSR, 1986, 37, N 2, 125-128
  作者：BORA, G.、BEU, L.、RUSSU, J.、BREAZU, D.、FARCASANU, I.、FABIAN, A.、TODOR, S.

  DOI：——

  日期：——
• ETHANOLAMINE-BASED LIPID BIOSYNTHETIC COMPOUNDS, METHOD OF MAKING AND USE THEREOF
  申请人：NOVAZOI THERANOSTICS

  公开号：US20170273995A1

  公开（公告）日：2017-09-28

  A method for treating cancer is disclosed. The method comprises administering to a subject in need thereof, an effective amount of a pharmaceutical composition comprising monoethanolamine, its prodrug or hybrid molecule or a pharmaceutically acceptable salt thereof, and a pharmaceutically effective carrier. Also disclosed is a composition comprising monoethanolamine or a pharmaceutically acceptable salt thereof and a pharmaceutically effective carrier, wherein the pharmaceutical composition is formulated for oral, intravenous, intraperitoneal, subcutaneous, dermal, or intranasal administration.
• Fluorophore-Labeled Cyclooxygenase-2 Inhibitors for the Imaging of Cyclooxygenase-2 Overexpression in Cancer: Synthesis and Biological Studies
  作者：Atul Bhardwaj、Jatinder Kaur、Frank Wuest、Edward E. Knaus

  DOI：10.1002/cmdc.201300355

  日期：2014.1

  (COX‐2)‐specific fluorescent cancer biomarkers were synthesized by linking the anti‐inflammatory drugs ibuprofen, (S)‐naproxen, and celecoxib to the 7‐nitrobenzofurazan (NBD) fluorophore. In vitro COX‐1/COX‐2 inhibition studies indicated that all of these fluorescent conjugates are COX‐2 inhibitors (IC50 range: 0.19–23.0 μM) with an appreciable COX‐2 selectivity index (SI≥4.3–444). In this study the celecoxib–NBD

  通过将抗炎药布洛芬，（S）-萘普生和塞来昔布与7-硝基苯并呋喃山（NBD）荧光团连接，合成了一组特定于环氧合酶2（COX-2）的荧光癌生物标记。体外COX-1 / COX-2抑制的研究表明，所有这些荧光缀合物的是COX-2抑制剂（IC 50范围：0.19-23.0μ中号）与可感知的COX-2选择性指数（SI≥4.3-444）。在这项研究中，塞来昔布-NBD共轭N-（2-（（7-硝基苯并[ c ] [1,2,5]恶二唑-4-基）氨基）乙基）-4-（5-（对甲苯基）- 3-（三氟甲基）-1 H-吡唑-1-基）苯磺酰胺（14），其显示的最高COX-2抑制的效力和选择性（COX-2的IC 50 = 0.19μ中号;使用COX-SI = 443.6），被认定为即将发生的COX-2特异性的生物标记用于癌症的荧光成像2表达人类结肠癌细胞系（HCA-7）。
• 10.1007/s11095-024-03747-6
  作者：Romani, Carola、Sponchioni, Mattia、Volonterio, Alessandro

  DOI：10.1007/s11095-024-03747-6

  日期：——

  Abstract Objective The development of an efficient, multifunctional drug delivery system overcoming different obstacles generally associated with drug formulations, including the poor accumulation of the active principle in the target site and its sustained release for prolonged time. Methods Our study proposes the development of a fluorinated poly(amidoamine) (PAMAM) carrier prodrug combining drug release boosted in alkaline environments with a possible implementation in 19F MRI applications. In particular, we functionalized the terminal primary amines of PAMAM G2 and G4 through an ad hoc designed fluorinated ibuprofen-arginine Michael acceptor to obtain multifunctional ibuprofen-PAMAM-Arg conjugates. Results These carriers demonstrated pH-dependent and sustained ibuprofen release for more than 5 days. This advantage was observed in both weak alkaline and physiological buffer solutions, allowing to overcome the limits associated to the burst release from similar fluorinated Arg-PAMAM dendrimers with ibuprofen physically encapsulated. Conclusion These findings, coupled to the high biocompatibility of the system, suggest a potential synergistic biomedical application of our conjugates, serving as vehicles for drug delivery and as 19F magnetic resonance imaging contrast agents.