L-谷氨酸二(2-丙烯基)酯对甲基苯磺酸盐 | 20845-16-3

• 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: L-谷氨酸二(2-丙烯基)酯对甲基苯磺酸盐
• 中文别名: L-谷氨酸二烯丙酯盐酸盐
• 英文名称: Diallyl glutamate p-toluenesulfonate
• 英文别名: diallyl L-glutamate p-toluenesulfonate；diallyl glutamate para-toluenesulfonic acid；diallyl glutamate-p-toluene-sulphonate；[(2S)-1,5-dioxo-1,5-bis(prop-2-enoxy)pentan-2-yl]azanium;4-methylbenzenesulfonate
• CAS: 20845-16-3
• 化学式: C₇H₈O₃S*C₁₁H₁₇NO₄
• 分子量: 399.465
• InChiKey: CXIWDQLHGWDUTO-FVGYRXGTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.79
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  141
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  L-谷氨酸二(2-丙烯基)酯对甲基苯磺酸盐 在 potassium hydrogen bifluoride 、 18-冠醚-6 、 sodium cyanoborohydride 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 水 、 溶剂黄146 、 甲苯 为溶剂， 反应 15.83h， 生成
  参考文献：
  名称：

  自焚氮芥子气前药用于自杀基因治疗。

  摘要：

  设计并合成了四种用于自杀基因疗法的新型潜在自焚前药，这些自焚前药来自苯酚和苯胺氮芥子气，衍生自其相应的氟乙基类似物的四种模型化合物，以及两种新的自我焚烧连接剂，称为GDEPT（基因指导的酶前药）治疗）。该自消灭性前药被设计为通过羧肽酶G2（CPG2）活化，通过不稳定的中间体通过1、6消除机制释放活性药物。因此，N-[（4-倒置问号[4-（双倒置问号2-氯乙基倒置问号氨基）苯氧基羰氧基]甲基倒置问号苯基）c氨基甲酰基] -L-谷氨酸（23），它们是双官能的烷基化剂，其中酚羟基或氨基官能团的活化作用通过氧羰基或氨基甲酰基键与本身通过氧羰基或氨基甲酰基键与谷氨酸连接的苄基间隔基掩盖。还合成了相应的氟乙基化合物25、32、42和44。基本原理是获得烷基化能力大大降低的模型化合物，与相应的氯乙基衍生物相比，它们与亲核试剂的反应性要低得多。这使得能够对作为CPG2底物的这些模型化合物进行研究，而不会产

  DOI：

  10.1021/jm980425k

文献信息

• [EN] ENZYME ACTIVATED SELF-IMMOLATIVE N-SUBSTITUTED NITROGEN MUSTARD PRODRUGS<br/>[FR] PROMEDICAMENTS ACTIVES PAR UNE ENZYME ET AUTO-IMMOLATEURS A BASE DE MOUTARDE D'AZOTE N-SUBSTITUTE
  申请人：CANCER REC TECH LTD

  公开号：WO2004020400A1

  公开（公告）日：2004-03-11

  This invention pertains to certain enzyme (CPG2) activated self-immolative nitrogen mustard prodrugs, which are useful in enzyme prodrug therapy (EPT), such as ADEPT and GDEPT, for the treatment of proliferative conditions, such as cancer, and which have the following formula: wherein RN is independently C1-7alkyl; X1 is independently -I, -Br, or Cl; X2 is independently -I, -Br, or -Cl; the group -N(CH2CH2X1)(CH2CH2X2) is independently attached at the 2-position or at the 4-position; each RG is independently -H or an ester substituent; n is independently an integer from 0 to 4; each RP, if present, is independently a phenyl substituent; m is independently an integer from 0 to 4; each RM, if present, is independently a mustard substituent; and pharmaceutically acceptable salts, solvates, amides, and esters thereof. The present invention also pertains to pharmaceutical compositions comprising such compounds; such compounds and compositions for use in methods of treatment of the human or animal body by therapy; the use of such compounds and compositions for the manufacture of medicaments for the treatment of proliferative conditions; and the like.

  本发明涉及一种特定的酶（CPG2）活化的自灭性亚硝基芥子前药，用于酶前药疗法（EPT），如ADEPT和GDEPT，用于治疗增殖性疾病，如癌症，并具有以下结构式：其中RN独立地是C1-7烷基；X1独立地是-I，-Br或Cl；X2独立地是-I，-Br或-Cl；该基团-N(CH2CH2X1)(CH2CH2X2)独立地连接在2位或4位；每个RG独立地是-H或酯基取代物；n独立地是0到4的整数；每个RP（如果存在）独立地是苯基取代物；m独立地是0到4的整数；每个RM（如果存在）独立地是芥子取代物；以及其药学上可接受的盐、溶剂化合物、酰胺和酯。本发明还涉及包含这种化合物的药物组合物；这种化合物和组合物用于通过治疗治疗人体或动物体的方法；这种化合物和组合物用于制造用于治疗增殖性疾病的药物；等等。
• DRUG LOADED POLYMERIC NANOPARTICLES AND METHODS OF MAKING AND USING SAME
  申请人：BIND Therapeutics, Inc.

  公开号：US20160354320A1

  公开（公告）日：2016-12-08

  The present disclosure generally relates to nanoparticles having about 0.2 to about 35 weight percent of a therapeutic agent; and about 10 to about 99 weight percent of biocompatible polymer such as a diblock poly(lactic) acid-poly(ethylene)glycol. Other aspects of the invention include methods of making such nanoparticles.

  本公开涉及大约0.2至大约35重量百分比的含有治疗剂的纳米颗粒；以及大约10至大约99重量百分比的生物相容性聚合物，例如双嵌段聚（乳酸）-聚（乙烯）乙二醇。该发明的其他方面包括制备这种纳米颗粒的方法。
• Pemetrexed Polymeric Nanoparticles And Methods Of Making And Using Same
  申请人：Pfizer Inc.

  公开号：US20170266187A1

  公开（公告）日：2017-09-21

  The present disclosure generally relates to nanoparticles having about 0.2 to about 35 weight percent of pemetrexed; and about 10 to about 99 weight percent of biocompatible polymer such as a diblock poly(lactic) acid-poly(ethylene)glycol. Other aspects of the invention include methods of making such nanoparticles.

  本公开涉及大约0.2至35重量％喷替芬的纳米颗粒；以及大约10至99重量％的生物相容性聚合物，例如双嵌段聚（乳酸）酸-聚（乙二醇）的聚合物。本发明的其他方面包括制备这种纳米颗粒的方法。
• Enzyme activated self-immolative n-substituted nitrogen mustard prodrugs
  申请人：Springer J Caroline

  公开号：US20060069154A1

  公开（公告）日：2006-03-30

  This invention pertains to certain enzyme (CPG2) activated self-immolative nitrogen mustard prodrugs, which are useful in enzyme prodrug therapy (EPT), such as ADEPT and GDEPT, for the treatment of proliferative conditions, such as cancer, and which have the following formula: wherein: R N is independently C 1-7 alkyl; X 1 is independently —I, —Br, or —Cl; X 2 is independently —I, —Br, or —Cl; the group —N(CH 2 CH 2 X 1 )(CH 2 CH 2 X 2 ) is independently attached at the 2-position or at the 4-position; each R G is independently —H or an ester substituent; n is independently an integer from 0 to 4; each R P , if present, is independently a phenyl substituent; m is independently an integer from 0 to 4; each R M , if present, is independently a mustard substituent; and pharmaceutically acceptable salts, solvates, amides, and esters thereof. The present invention also pertains to pharmaceutical compositions comprising such compounds; such compounds and compositions for use in methods of treatment of the human or animal body by therapy; the use of such compounds and compositions for the manufacture of medicaments for the treatment of proliferative conditions; and the like.

  本发明涉及某些酶（CPG2）活化的自我毁灭性亚硝基芥前药，其在酶前药疗法（EPT）如ADEPT和GDEPT中有用，用于治疗增殖性疾病，如癌症，其化学式如下：其中：RN独立地是C1-7烷基；X1独立地是—I，—Br或—Cl；X2独立地是—I，—Br或—Cl；—N(CH2CH2X1)(CH2CH2X2)基团独立地连接在2位或4位；每个RG独立地是—H或酯基取代基；n独立地是0到4的整数；每个RP（如存在）独立地是苯基取代基；m独立地是0到4的整数；每个RM（如存在）独立地是芥子气取代基；以及其药学上可接受的盐，溶剂化合物，酰胺和酯。 本发明还涉及包含这种化合物的制药组合物；这种化合物和组合物用于治疗人体或动物体的治疗方法；使用这种化合物和组合物制造治疗增殖性疾病药物等。
• Dendritic Polyglutamic Porphyrins: Probing Porphyrin Protection by Oxygen-Dependent Quenching of Phosphorescence
  作者：Sergei A. Vinogradov、Leu-Wei Lo、David F. Wilson

  DOI：10.1002/(sici)1521-3765(19990401)5:4<1338::aid-chem1338>3.0.co;2-n

  日期：1999.4.1

  A series of dendritic polyglutamic Pd porphyrins with a Pd-meso-tetra-4-carboxyphenylporphyrin (PdTCPP) core was synthesized by the divergent growth approach. The synthesized compounds are described by the general formula PdPorphGlu(N)OR, where N=1-4 (dendrimer generation), Glu=glutamate layer, and R is the terminal group=H, All (allyl), Et, or Bz. Additionally, 11-aminoundecanoic acid (AUDA) was added to the periphery of PdPorphGlu(1)OH to give PdPorphGlu(1)AUDAOH, which was, in turn, modified with another layer of glutamates, to give the pseudodendrimer PdPorphGlu(1)AUDAGlu(1)OH. All the synthesized compounds phosphoresce strongly with lambda(max) = 690 nm and lifetimes in the range of 0.5-1 ms in deoxygenated solutions. The observed phosphorescence is quenched by O-2, and the corresponding Stern - Volmer plots have been determined for the series of synthesized compounds in DMF and H2O solutions. In DMF there was almost no difference in the quenching constants (K-q) for all the synthesized compounds; however, in water the values of K-q decreased significantly as the size of the dendrimers increased. We suggest that, depending on the solvent properties, the polyglutamic branches adopt either open or compact conformations. This alters the barrier to oxygen diffusion towards the porphyrin core.