Benzyl 2-[2-hydroxyethyl-(2-oxo-2-phenylmethoxyethyl)amino]acetate | 51992-85-9

• 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: Benzyl 2-[2-hydroxyethyl-(2-oxo-2-phenylmethoxyethyl)amino]acetate
• CAS: 51992-85-9
• 化学式: C₂₀H₂₃NO₅
• 分子量: 357.406
• InChiKey: MTHQGXSGOLGIJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  26
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Benzyl 2-[2-hydroxyethyl-(2-oxo-2-phenylmethoxyethyl)amino]acetate 在 吡啶 、 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 乙酸酐 、 potassium carbonate 、 三苯基膦 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 乙腈 为溶剂， 反应 96.08h， 生成 22-(2-((2-(bis(2-(benzyloxy)-2-oxoethyl)amino)ethyl)(2-methoxy-2-oxoethyl)amino)ethyl)-2,2-dimethyl-4,20-dioxo-3,9,12,15-tetraoxa-5,19,22-triazatetracosan-24-oic acid
  参考文献：
  名称：

  Controlling Multivalency and Multimodality: Up to Pentamodal Dendritic Platforms Based on Diethylenetriaminepentaacetic Acid Cores

  摘要：

  A highly versatile synthetic strategy is described to generate multimodal and multivalent platforms based on a diethylenetriaminepentaacetic (DTPA) core. Compounds with different functionalization patterns, from mono- to pentamodal, have been prepared using robust and simple chemistry.

  DOI：

  10.1021/ol500022n
• 作为产物：
  描述：

  C.I.酸性橙108 、 2-溴乙酸苄酯 在 potassium hydrogencarbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 Benzyl 2-[2-hydroxyethyl-(2-oxo-2-phenylmethoxyethyl)amino]acetate
  参考文献：
  名称：

  一类1,4,7-三氮杂环壬烷衍生物作为耗铁抗肿瘤剂的合成与评价

  摘要：

  铁消耗已被确认为治疗癌症的有效策略。在当前的研究中，一系列1,4,7-三氮杂环壬烷衍生物HE-NO2A，HP-NO2A和NE2P2A，以及双功能螯合剂p -NO 2 -PhPr-NE3TA和p -NH 2合成了-PhPr-NE3TA，并将其作为铁消耗剂进行评估，以用于潜在的抗人肝细胞癌抗癌治疗。使用肝细胞癌细胞测量了这些螯合剂的细胞毒性，并与临床上可用的铁耗竭剂DFO和通用金属螯合剂DTPA进行了比较。所有这些1,4,7-三氮杂环壬烷基螯合剂均比DFO和DTPA表现出更强的抗增殖活性。其中，以对-NO 2 -PhPr-NE3TA和对-NH 2为代表的具有苯丙基侧链的螯合剂。-PhPr-NE3TA对HepG2细胞显示出最高的抗增殖活性。因此，这些化合物作为潜在的抗癌疗法中的铁耗竭剂，是进行高级研究的诱人候选物，并且可以与靶向部分进一步结合，以用于靶向铁耗竭疗法的未来发展。

  DOI：

  10.1016/j.bmcl.2017.11.048

文献信息

• Stable Aziridinium Salts as Versatile Intermediates: Isolation and Regio- and Stereoselective Ring-Opening and Rearrangement
  作者：Hyun A. Song、Mamta Dadwal、Yeseul Lee、Emily Mick、Hyun-Soon Chong

  DOI：10.1002/anie.200805244

  日期：2009.2.2

  Rock trapping and exploration: Aziridinium bromide salts were discovered serendipitously during bromination of N,N‐dicarboxymethylated β‐amino alcohols. Regiospecific ring‐opening and rearrangement of the isolated, surprisingly stable aziridinium salts produces useful molecules including C‐functionalized oxomorpholines and α,β‐unsaturated amines.

  岩石捕获和勘探：在N，N-二羧甲基化的β-氨基醇的溴化过程中偶然发现了氮丙啶鎓盐。区域特异性的开环和重排，分离出的稳定的叠氮鎓盐可产生有用的分子，包括C-官能化的吗啉和α，β-不饱和胺。
• Tumor-targeted optical contrast agents
  申请人：MALLINCKRODT INC.

  公开号：US20040141920A1

  公开（公告）日：2004-07-22

  Cyanine dye bioconjugates useful for diagnostic imaging and therapy are disclosed. The conjugates include several cyanine dyes with a variety of bis- and tetrakis (carboxylic acid) homologs. The compounds may be conjugated to bioactive peptides, carbohydrates, hormones, drugs, or other bioactive agents. The small size of the compounds allows more favorable delivery to tumor cells as compared to larger molecular weight imaging agents. The various dyes are useful over the range of 350 to 1300 nm, the exact range being dependent upon the particular dye. The use of dimethylsulfoxide helps to maintain the fluorescence of the compounds. The inventive compounds are useful for diagnostic imaging and therapy, in endoscopic applications for the detection of tumors and other abnormalities, for localized therapy, for photoacoustic tumor imaging, detection and therapy, and for sonofluoresence tumor imaging, detection and therapy.

  揭示了用于诊断成像和治疗的青菁染料生物共轭物。这些共轭物包括几种青菁染料，具有各种双和四(羧酸)同系物。这些化合物可以与生物活性肽、碳水化合物、激素、药物或其他生物活性剂结合。与分子量较大的成像试剂相比，这些化合物的小尺寸使其更有利于输送到肿瘤细胞。各种染料在350到1300纳米范围内是有用的，确切范围取决于特定的染料。二甲基亚砜的使用有助于保持化合物的荧光。这些创新的化合物在诊断成像和治疗中很有用，用于内窥镜应用以检测肿瘤和其他异常，用于局部治疗，用于光声肿瘤成像、检测和治疗，以及用于声荧光肿瘤成像、检测和治疗。
• Efficient synthesis and evaluation of bimodal ligand NETA
  作者：Hyun-Soon Chong、Hyun A. Song、Noah Birch、Thien Le、Sooyoun Lim、Xiang Ma

  DOI：10.1016/j.bmcl.2008.03.084

  日期：2008.6

  The efficient and short synthetic route to the structurally novel bimodal ligand NETA for antibody-targeted radiation therapy (radioimmunotherapy, RIT) of cancer was developed. The structure of NETA was determined by X-ray crystallography. The arsenazo-based UV spectroscopic complexation kinetics data suggest that NETA is a promising chelator for use in RIT applications of (212)Bi, (213)Bi, and (177)Lu. (c) 2008 Published by Elsevier Ltd.
• Synthesis of enantiomerically pure diethylenetriaminepentaacetic acid analogs. L-Phenylalanine as the educt for substitution at the central acetic acid
  作者：Matthew A. Williams、Henry Rapoport

  DOI：10.1021/jo00057a030

  日期：1993.2

  The enantiospecific synthesis of diethylenetriaminepentaacetic acid (DTPA) analogues from L-phenylalanine via a bis N-alkylation strategy is described. N-Alkylation of p-nitrophenylalanine benzyl ester (4) occurs readily with dibenzyl and di-tert-butyl [N-(bromoethyl)amino]diacetates 5a and 5b using a phosphate buffer/acetonitrile reaction medium. N,N-Dialkyl (2a,2b) and N-monoalkyl (3a, 3b) derivatives Of L-p-nitrophenylalanine thus are obtained directly in a single operation. Subjecting the monoalkylated material, N-(ethylamino) diacetic acid di-tert-butyl ester 3b, to a second alkylation with dibenzyl bromoethylaminediacetate 5a affords mixed pentaester 2c in which the terminal carboxyl groups are differentiated as benzyl esters at one end and tert-butyl at the other. Both complete and selective deprotections of the differentiated carboxyl groups in pentaesters 2a, 2b, and 2c are possible, allowing specific control of the carboxyl functionality at each terminus. The enantiomeric composition of monoalkyl amino acids 3a and 3b was evaluated by derivatizing with (+)-alpha-methylbenzyl isocyanate to afford the corresponding ureas. Analysis of the ureas by HPLC established the enantiomeric purity in each case as >99 %, thereby also establishing the enantiomeric purity of dialkyl compounds as >99 %. Pentaacid 2d readily forms an optically active metal chelate with yttrium(III) as a single diastereomer.
• Synthesis and evaluation of a class of 1,4,7-triazacyclononane derivatives as iron depletion antitumor agents
  作者：Sheng Wang、Yongkang Gai、Shasha Zhang、Lei Ke、Xiang Ma、Guangya Xiang

  DOI：10.1016/j.bmcl.2017.11.048

  日期：2018.1

  Iron depletion has been confirmed as an efficient strategy for cancer treatment. In the current study, a series of 1,4,7-triazacyclononane derivatives HE-NO2A, HP-NO2A and NE2P2A, as well as the bifunctional chelators p-NO2-PhPr-NE3TA and p-NH2-PhPr-NE3TA were synthesized and evaluated as iron-depleting agents for the potential anti-cancer therapy against human hepatocellular carcinoma. The cytotoxicity

  铁消耗已被确认为治疗癌症的有效策略。在当前的研究中，一系列1,4,7-三氮杂环壬烷衍生物HE-NO2A，HP-NO2A和NE2P2A，以及双功能螯合剂p -NO 2 -PhPr-NE3TA和p -NH 2合成了-PhPr-NE3TA，并将其作为铁消耗剂进行评估，以用于潜在的抗人肝细胞癌抗癌治疗。使用肝细胞癌细胞测量了这些螯合剂的细胞毒性，并与临床上可用的铁耗竭剂DFO和通用金属螯合剂DTPA进行了比较。所有这些1,4,7-三氮杂环壬烷基螯合剂均比DFO和DTPA表现出更强的抗增殖活性。其中，以对-NO 2 -PhPr-NE3TA和对-NH 2为代表的具有苯丙基侧链的螯合剂。-PhPr-NE3TA对HepG2细胞显示出最高的抗增殖活性。因此，这些化合物作为潜在的抗癌疗法中的铁耗竭剂，是进行高级研究的诱人候选物，并且可以与靶向部分进一步结合，以用于靶向铁耗竭疗法的未来发展。