D-天门冬氨酸苄酯对甲苯磺酸盐 | 4079-64-5

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 天然氨基酸及其衍生物
• 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
• 中文名称: D-天门冬氨酸苄酯对甲苯磺酸盐
• 中文别名: DL-对硝基苯丙氨酸(一水物)；D-天冬氨酸双苄酯对甲苯磺酸盐
• 英文名称: D-aspartic acid dibenzyl ester toluene-p-sulfonate
• 英文别名: (R)-dibenzyl 2-aminosuccinate p-tolyl sulfonic acid；(R)-dibenzyl 2-aminosuccinate p-toluenesulfonic acid salt；D-aspartic acid dibenzyl ester p-toluenesulfonate；(D)-H-Asp-(OBn)-OBn*p-TsOH；(R)-aspartic acid dibenzylester p-toluenesulfonate；D-aspartate dibenzylester p-toluenesulfonate；(D)-Asp-(OBn)₂*p-TsOH；H-D-Asp(OBzl)-OBzl•TosOH；Asp(OBz)₂ p-TSA；R-aspartic acid dibenzyl ester p-tosylate；(R)-dibenzyl 2-aminosuccinate tosylate；H-D-asp(OBzl)-OBzl p-tosylate；dibenzyl L-aspartate*p-TsOH；D-Asp(OBn)-OBn*p-TsOH salt；(D)-aspartic acid dibenzyl ester 4-toluenesulfonic acid；(D)-aspartic acid dibenzyl ester 4-toluenesulfonate；L-aspartic acid dibenzyl ester p-toluenesulfonate；(r)-Dibenzyl 2-aminosuccinate 4-methylbenzenesulfonate；dibenzyl (2R)-2-aminobutanedioate;4-methylbenzenesulfonic acid
• CAS: 4079-64-5
• 化学式: C₇H₈O₃S*C₁₈H₁₉NO₄
• mdl: MFCD00035102
• 分子量: 485.558
• InChiKey: HLMUYZYLPUHSNV-PKLMIRHRSA-N

物化性质

• 熔点：
  155-158℃
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  2.52
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  146
• 氢给体数：
  1
• 氢受体数：
  7

安全信息

• 海关编码：
  2923900090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  D-天门冬氨酸苄酯对甲苯磺酸盐 在 4-二甲氨基吡啶 、 叔丁基氯化镁 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 33.0h， 生成 (2R)-benzyl N-(tert-butyldimethylsilyl)-4-oxoazetidine-2-carboxylate
  参考文献：
  名称：

  Cundy, Darren J.; Donohue, Andrew C.; McCarthy, Tom D., Journal of the Chemical Society. Perkin transactions I, 1999, # 5, p. 559 - 567

  摘要：

  DOI：
• 作为产物：
  描述：

  D-天门冬氨酸 、 对甲苯磺酸 、 苯甲醇 以 苯 为溶剂， 反应 7.0h， 以94%的产率得到D-天门冬氨酸苄酯对甲苯磺酸盐
  参考文献：
  名称：

  Tryptophan-containing dipeptide derivatives as potent PPARγ antagonists: Design, synthesis, biological evaluation, and molecular modeling

  摘要：

  The discovery of peroxisome proliferator-activated receptor gamma (PPAR gamma) antagonists (also termed "selective PPAR gamma modulators, SPPAR gamma M") is now of a great interest in the treatment of diabetes and obesity. The structure of compound la (G3335, Fig. 1), a novel class of PPAR gamma antagonist, is entirely different from that of other reported PPAR gamma antagonists. A series of 35 novel analogues (1b-1, 9a-d, 13a-t) were designed, synthesized and evaluated against the agonistic effects exerted by rosiglitazone. These results indicated that most functional groups of la were conserved, and six new compounds (1b, 1c, and 9a-d) exhibited strong PPAR gamma antagonistic activities (IC50 values of 5.2-25.8 mu M) against 10 mu M rosiglitazone in the promotion of the PPAR gamma-LBD-CBP (ligand-binding domain and cAMP-response-element binding protein) interaction as investigated by yeast two-hybrid technology based assay. Molecular modeling studies for compounds 1a-d, 1h, 9c-d, and 13a were also presented. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.01.032

文献信息

• Total Synthesis of the Antiviral Peptide Antibiotic Feglymycin
  作者：Frank Dettner、Anne Hänchen、Dominique Schols、Luigi Toti、Antje Nußer、Roderich D. Süssmuth

  DOI：10.1002/anie.200804130

  日期：2009.2.23

  An adaptable approach: The first highly convergent stereoselective synthesis of feglymycin (see structure) and its enantiomer is based on the coupling of repeating peptide fragments. The use of weakly basic conditions throughout the synthesis suppressed the epimerization of sensitive aryl glycine units. Feglymycin has strong anti‐HIV activity as well as potent (previously identified as weak) antibacterial

  一种适应性强的方法：Feglymycin（见结构）及其对映异构体的第一个高度收敛的立体选择性合成是基于重复肽片段的偶联。在整个合成过程中使用弱碱性条件抑制了敏感的芳基甘氨酸单元的差向异构化。Feglymycin具有强大的抗HIV活性以及对金黄色葡萄球菌的有效（先前被确认为弱）抗菌活性。
• [EN] COMPOSITIONS AND METHODS FOR ASSESSING EYE VASCULATURE<br/>[FR] COMPOSITIONS ET MÉTHODES POUR ÉVALUER LE SYSTÈME VASCULAIRE DE L'ŒIL
  申请人：MEDIBEACON INC

  公开号：WO2016183351A1

  公开（公告）日：2016-11-17

  The present disclosure relates to compositions and methods for assessing blood vessels and organs of the body, more specifically to methods for assessing the vasculature of the eye.

  本公开涉及用于评估人体血管和器官的组合物和方法，更具体地说是用于评估眼部血管的方法。
• METHODS FOR RENAL FUNCTION DETERMINATION
  申请人：MediBeacon Inc.

  公开号：US20190125902A1

  公开（公告）日：2019-05-02

  The present disclosure relates to systems and methods for determining the renal glomerular filtration rate or assessing the renal function in a patient in need thereof. The method includes administering a pyrazine compound of Formula I to a patient and monitoring the rate in which the kidneys of the patient eliminate the pyrazine from the systemic circulation of the patient. The pyrazine compound fluoresces when exposed to electromagnetic radiation which is detected using one or more sensors. The rate in which the fluorescence decreases in the patient is used to calculate the renal glomerular filtration rate in the patient.

  本公开涉及用于确定肾小球滤过率或评估患者肾功能的系统和方法。该方法包括向患者施用化合物I的吡嗪类化合物，并监测患者的肾脏从患者的全身循环中排除吡嗪的速率。当暴露于电磁辐射时，吡嗪化合物会发出荧光，使用一个或多个传感器来检测。患者体内荧光减少的速率被用来计算患者的肾小球滤过率。
• COMPOSITIONS AND SYSTEMS FOR RENAL FUNCTION DETERMINATION
  申请人：MediBeacon Inc.

  公开号：US20190125901A1

  公开（公告）日：2019-05-02

  The present disclosure relates to systems and methods for determining the renal glomerular filtration rate or assessing the renal function in a patient in need thereof. The system includes a computing device, a power supply, one or more sensors, and at least one tracer agent that fluoresces when exposed to electromagnetic radiation. The electromagnetic radiation is detected using the sensors, and the rate in which the fluorescence decreases in the patient is used to calculate the renal glomerular filtration rate in the patient.

  本公开涉及确定肾小球滤过率或评估需要的患者的肾功能的系统和方法。该系统包括计算设备、电源、一个或多个传感器，以及至少一种示踪剂，当暴露于电磁辐射时发出荧光。传感器检测电磁辐射，患者体内荧光减弱的速率用于计算患者的肾小球滤过率。
• Synthesis and Biological Evaluation of Novel 10-Substituted-7-ethyl-10-hydroxycamptothecin (SN-38) Prodrugs
  作者：Mo Zhou、Meixia Liu、Xinhua He、Hong Yu、Di Wu、Yishan Yao、Shiyong Fan、Ping Zhang、Weiguo Shi、Bohua Zhong

  DOI：10.3390/molecules191219718

  日期：——

  In an attempt to improve the antitumor activity and reduce the side effects of irinotecan (2), novel prodrugs of SN-38 (3) were prepared by conjugating amino acids or dipeptides to the 10-hydroxyl group of SN-38 via a carbamate linkage. The synthesized compounds completely generated SN-38 in pH 7.4 buffer or in human plasma, while remaining stable under acidic conditions. All prodrug compounds demonstrated much greater in vitro antitumor activities against HeLa cells and SGC-7901 cells than irinotecan. The most active compounds, 5h, 7c, 7d, and 7f, exhibited IC50 values that were 1000 times lower against HeLa cells and 30 times lower against SGC-7901 cells than those of irinotecan, and the inhibitory activities of these prodrugs against acetylcholinesterase (AchE) were significantly reduced, with IC50 values more than 6.8 times greater than that of irinotecan. In addition, compound 5e exhibited the same level of tumor growth inhibitory activity as irinotecan (CPT-11) in a human colon xenograft model in vivo.

  为了提高伊立替康（irinotecan, 2）的抗肿瘤活性并减少其副作用，研究人员通过羧酸酯链接将氨基酸或二肽与SN-38（3）的10-羟基结合，制备了新型的SN-38前药。这些合成的化合物在pH 7.4的缓冲液或人血浆中能够完全生成SN-38，同时在酸性条件下保持稳定。所有前药化合物在体外对HeLa细胞和SGC-7901细胞的抗肿瘤活性都明显高于伊立替康。最活跃的化合物5h、7c、7d和7f，在HeLa细胞中的IC50值比伊立替康低1000倍，而在SGC-7901细胞中的IC50值低30倍，同时这些前药对乙酰胆碱酯酶（AchE）的抑制活性显著降低，IC50值比伊立替康高出6.8倍。此外，化合物5e在体内的人类结肠异种移植模型中表现出与伊立替康（CPT-11相同的肿瘤生长抑制活性。