4-((2-(2-(2-azidoethoxy)ethoxy)ethyl)amino)-4-oxobutanoic acid | 1189096-56-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4-((2-(2-(2-azidoethoxy)ethoxy)ethyl)amino)-4-oxobutanoic acid
• 英文别名: N3-DOOA-Suc-OH；4-[2-[2-(2-azidoethoxy)ethoxy]ethylamino]-4-oxobutanoic acid
• CAS: 1189096-56-7
• 化学式: C₁₀H₁₈N₄O₅
• 分子量: 274.277
• InChiKey: MWLLWUKYEXBSBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  19
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  99.2
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-((2-(2-(2-azidoethoxy)ethoxy)ethyl)amino)-4-oxobutanoic acid 在 4-二甲氨基吡啶 、 copper(II) sulfate 、 sodium ascorbate 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 24.0h， 生成 (1'S,2R,2'S,4'S,5R,7'S,8'R,9'S,12'S,13'R,16'S)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-18'-en-16'-yl 3-[2-(2-[2-(4-(4-[(1E,3Z,6E)-3-hydroxy-7-(4-hydroxy-3-methoxyphenyl)-5-oxohepta-1,3,6-trien-1-yl]-2-methoxyphenoxymethyl)-1H-1,2,3-triazol-1-yl)ethoxy]ethoxy)ethylcarbamoyl]propanoate
  参考文献：
  名称：

  Bivalent ligands incorporating curcumin and diosgenin as multifunctional compounds against Alzheimer’s disease

  摘要：

  In an effort to combat the multifaceted nature of Alzheimer's disease (AD) progression, a series of multifunctional, bivalent compounds containing curcumin and diosgenin were designed, synthesized, and biologically characterized. Screening results in MC65 neuroblastoma cells established that compound 38 with a spacer length of 17 atoms exhibited the highest protective potency with an EC50 of 111.7 +/- 9.0 nM. A reduction in protective activity was observed as spacer length was increased up to 28 atoms and there is a clear structural preference for attachment to the methylene carbon between the two carbonyl moieties of curcumin. Further study suggested that antioxidative ability and inhibitory effects on amyloid-b oligomer (A beta O) formation may contribute to the neuroprotective outcomes. Additionally, compound 38 was found to bind directly to A beta, similar to curcumin, but did not form complexes with the common biometals Cu, Fe, and Zn. Altogether, these results give strong evidence to support the bivalent design strategy in developing novel compounds with multifunctional ability for the treatment of AD. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.10.032
• 作为产物：
  描述：

  1,8-二叠氮基-3,5-二氧杂辛烷 在 盐酸 、 三乙胺 、 三苯基膦 作用下， 以 乙醚 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 生成 4-((2-(2-(2-azidoethoxy)ethoxy)ethyl)amino)-4-oxobutanoic acid
  参考文献：
  名称：

  Bivalent ligands incorporating curcumin and diosgenin as multifunctional compounds against Alzheimer’s disease

  摘要：

  In an effort to combat the multifaceted nature of Alzheimer's disease (AD) progression, a series of multifunctional, bivalent compounds containing curcumin and diosgenin were designed, synthesized, and biologically characterized. Screening results in MC65 neuroblastoma cells established that compound 38 with a spacer length of 17 atoms exhibited the highest protective potency with an EC50 of 111.7 +/- 9.0 nM. A reduction in protective activity was observed as spacer length was increased up to 28 atoms and there is a clear structural preference for attachment to the methylene carbon between the two carbonyl moieties of curcumin. Further study suggested that antioxidative ability and inhibitory effects on amyloid-b oligomer (A beta O) formation may contribute to the neuroprotective outcomes. Additionally, compound 38 was found to bind directly to A beta, similar to curcumin, but did not form complexes with the common biometals Cu, Fe, and Zn. Altogether, these results give strong evidence to support the bivalent design strategy in developing novel compounds with multifunctional ability for the treatment of AD. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.10.032

文献信息

• [EN] PROGRAMMABLE POLYMERIC DRUGS<br/>[FR] MÉDICAMENTS POLYMÈRES PROGRAMMABLES
  申请人：SONY CORP

  公开号：WO2019071208A1

  公开（公告）日：2019-04-11

  Compounds useful as biologically active compounds are disclosed. The compounds have the following structure (I): or a stereoisomer, tautomer or salt thereof, wherein R1, R2, R3, L, L1, L2, L3, M and n are as defined herein. Methods associated with preparation and use of such compounds is also provided.

  披露了作为生物活性化合物有用的化合物。这些化合物具有以下结构（I）：或其立体异构体、互变异构体或盐，其中R1、R2、R3、L、L1、L2、L3、M和n如本文所定义。还提供了与这些化合物的制备和使用相关的方法。
• [EN] PROGRAMMABLE DENDRITIC DRUGS<br/>[FR] MÉDICAMENTS DENDRITIQUES PROGRAMMABLES
  申请人：SONY CORP

  公开号：WO2019071153A1

  公开（公告）日：2019-04-11

  Compounds useful as biologically active compounds are disclosed. The compounds have the following structure (I) or a stereoisomer, tautomer or salt thereof, wherein R1, R2, R3, L, L1, L2, L3, L4, L5, L6, M, m, and p are as defined herein. Methods associated with preparation and use of such compounds is also provided.

  披露了作为生物活性化合物有用的化合物。这些化合物具有以下结构（I）或其立体异构体、互变异构体或盐，其中R1、R2、R3、L、L1、L2、L3、L4、L5、L6、M、m和p如本文所定义。还提供了与这些化合物的制备和使用相关的方法。
• [EN] POLYMERS WITH RIGID SPACING GROUPS COMPRISING BIOLOGICALLY ACTIVE COMPOUNDS<br/>[FR] POLYMÈRES À GROUPES D'ESPACEMENT RIGIDES COMPRENANT DES COMPOSÉS BIOLOGIQUEMENT ACTIFS
  申请人：SONY CORP

  公开号：WO2019140301A1

  公开（公告）日：2019-07-18

  Compounds useful as biologically active compounds are disclosed. The compounds have the following structure (I): or a stereoisomer, tautomer or salt thereof, wherein A, R1, R2, R3, R4, R5, L, L1, L2, L3, L4, M, m and n are as defined herein. Methods associated with preparation and use of such compounds is also provided.

  揭示了作为生物活性化合物有用的化合物。这些化合物具有以下结构（I）：或其立体异构体、互变异构体或盐，其中A、R1、R2、R3、R4、R5、L、L1、L2、L3、L4、M、m和n如本文所定义。还提供了与这些化合物的制备和使用相关的方法。
• Programmable polymeric drugs
  申请人：Sony Corporation

  公开号：US11312736B1

  公开（公告）日：2022-04-26

  Compounds useful as biologically active compounds are disclosed. The compounds have the following structure (I): or a stereoisomer, tautomer or salt thereof, wherein R1, R2, R3, L, L1, L2, L3, M and n are as defined herein. Methods associated with preparation and use of such compounds is also provided.

  本研究公开了可用作生物活性化合物的化合物。这些化合物具有以下结构 (I)： 或其立体异构体、同系物或盐，其中 R1、R2、R3、L、L1、L2、L3、M 和 n 如本文所定义。还提供了与制备和使用此类化合物相关的方法。
• β-Lactam-based approach for the chemical programming of aldolase antibody 38C2
  作者：Julia I. Gavrilyuk、Ulrich Wuellner、Carlos F. Barbas

  DOI：10.1016/j.bmcl.2009.01.028

  日期：2009.3

  Irreversible chemical programming of monoclonal aldolase antibody (mAb) 38C2 has been accomplished with beta-lactam-equipped targeting modules. A model study was first performed with beta-lactam conjugated to biotin. This conjugate efficiently and selectively modified the catalytic site lysine (LysH93) of mAb 38C2. We then conjugated a beta-lactam to a cyclic-RGD peptide to chemically program mAb 38C2 to target integrin receptors alpha(nu)beta(3) and alpha(nu)beta(5). The chemically programmed antibody bound specifically to the isolated integrin receptor proteins as well as the integrins expressed on human melanoma cells. This approach provides an efficient and versatile solution to irreversible chemical programming of aldolase antibodies. (C) 2009 Elsevier Ltd. All rights reserved.