(R)-(-)-n-(苯基磺酰基)谷氨酸 | 20531-36-6

• 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: (R)-(-)-n-(苯基磺酰基)谷氨酸
• 中文别名: (-)-N-(苯磺酰)谷氨酸
• 英文名称: 2-(benzenesulfonyl)-L-glutamic acid
• 英文别名: N-benzenesulfonyl-L-glutamic acid；N-benzenesulfonyl-glutamic acid；N-benzesulfonyl-L-glutamic acid；N-benzenesulfonyl-L-glutamic acid；Bs-gluH；bsgluH2；(2S)-2-(benzenesulfonamido)pentanedioic acid
• CAS: 20531-36-6
• 化学式: C₁₁H₁₃NO₆S
• mdl: MFCD00066326
• 分子量: 287.293
• InChiKey: PJLOGZZDKDUMFU-VIFPVBQESA-N

物化性质

• 熔点：
  137-140 °C(lit.)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  129
• 氢给体数：
  3
• 氢受体数：
  7

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2935009090

反应信息

• 作为反应物：
  描述：

  (R)-(-)-n-(苯基磺酰基)谷氨酸 在 PPA 作用下， 反应 2.0h， 生成
  参考文献：
  名称：

  De, A. U.; Pandey, Jiten; Majumdar, Anjali, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1982, vol. 21, # 5, p. 481 - 483

  摘要：

  DOI：
• 作为产物：
  描述：

  在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到(R)-(-)-n-(苯基磺酰基)谷氨酸
  参考文献：
  名称：

  N-Substituted Glutamyl Sulfonamides as Inhibitors of Glutamate Carboxypeptidase II (GCP2)

  摘要：

  Glutamate carboxypeptidase II (GCP2) is a membrane‐bound cell‐surface peptidase which is implicated in several neurological disorders and is also over‐expressed in prostate tumor cells. There is a significant interest in the inhibition of GCP2 as a means of neuroprotection, while GCP2 inhibition as a method to treat prostate cancer remains a topic of further investigation. The key zinc‐binding functional group of the well‐characterized classes of GCP2 inhibitors (phosphonates and phosphoramidates) is tetrahedral and negatively charged at neutral pH, while glutamyl urea class of inhibitors possesses a planar and neutral zinc‐binding group. This study introduces a new class of GCP2 inhibitors, N‐substituted glutamyl sulfonamides, which possess a neutral tetrahedral zinc‐binding motif. A library containing 15 secondary sulfonamides and 4 tertiary (N‐methyl) sulfonamides was prepared and evaluated for inhibitory potency against purified GCP2 enzyme activity. While most inhibitors lacked potency at 100 μm, short alkyl sulfonamides exhibited promising low micromolar potency, with the optimal inhibitor in this series being glutamyl N‐(propylsulfonamide) (2g). Lastly, molecular docking was used to develop a model to formulate an explanation for the relative inhibitory potencies employed for this class of inhibitors.

  DOI：

  10.1111/j.1747-0285.2011.01085.x

文献信息

• [EN] PROCESS FOR PREPARING OPTICALLY ACTIVE CETIRIZINE OR ITS SALT<br/>[FR] PROCEDE DE PREPARATION DE CETIRIZINE OPTIQUEMENT ACTIVE OU DE SON SEL
  申请人：HANLIM PHARMACEUTICAL CO LTD

  公开号：WO2005073207A1

  公开（公告）日：2005-08-11

  Provided are a process for preparing optically active cetirizine or its salt from racemic cetirizine or its salt using glutamate of 2-[2-[4-[(4-chlorphenyl)phenylmethyl]-1-piperazinyl] ethoxy]acetic ester and the glutamate of 2-[2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl] ethoxy]acetic ester useful as an intermediate for the preparation of the optically active cetirizine or its salt.

  提供了一种从左旋西替利嗪或其盐制备光学活性西替利嗪或其盐的方法，使用2-[2-[4-[(4-氯苯基)苯甲基]-1-哌嗪基]乙氧基]乙酸酯的谷氨酸盐和2-[2-[4-[(4-氯苯基)苯甲基]-1-哌嗪基]乙氧基]乙酸酯的谷氨酸盐，作为制备光学活性西替利嗪或其盐的中间体。
• Synthesis, screening and quantitative structure–activity relationship (QSAR) studies of some glutamine analogues for possible anticancer activity
  作者：K. Srikanth、Ch.Anil Kumar、Balaram Ghosh、Tarun Jha

  DOI：10.1016/s0968-0896(02)00079-2

  日期：2002.7

  benzene ring. The synthesized compounds have been tested for antitumor activity against Ehrlich ascites carcinoma (EAC) in Swiss albino mice using percentage inhibition of tumor weight as inhibitory parameter. In order to elucidate the structural requirements for antitumor activity, quantitative structure-activity relationship (QSAR) studies have been performed using extra thermodynamic model of Hansch

  我们描述了36种具有不同取代基的新型5-n-取代-2-（取代苯磺酰基）谷氨酰胺6-41的合成，生物学活性和QSAR研究。这些化合物被设计为大多数反应性氨基酸“谷氨酰胺”（GLN）的结构类似物，尤其是在肿瘤细胞中。他们提出了在R（5）位置的新基本侧链以及苯环上2'，3'，4'和5'位置的不同取代基。已使用肿瘤重量的百分比抑制作为抑制参数，对合成的化合物在瑞士的白化病小鼠中测试了针对艾氏腹水癌（EAC）的抗肿瘤活性。为了阐明抗肿瘤活性的结构要求，已经使用Hansch的额外热力学模型进行了定量构效关系（QSAR）研究。QSAR方程表明，芳香环系统的电子参数（sigma），空间参数（Es）以及脂族侧链上取代基（L）的甾醇长度在一定程度上与抗肿瘤活性相关。共振因子在芳香环体系中对活性的主要电子贡献。
• Possible anticancer agents: synthesis, pharmacological activity, and molecular modeling studies on some 5-N -Substituted-2-N-(substituted benzenesulphonyl)-L(+)Glutamines
  作者：Tarun Jha、Soumya Basu、Amit Kumar Halder、Nilanjan Adhikari、Soma Samanta

  DOI：10.1007/s00044-017-1858-1

  日期：2017.7

  On the basis of our earlier work, fortyone 5-N-substituted-2N-(substituted benzenesulphonyl)-L(+)glutamines were synthesized and screened for cancer cell inhibitory activity. The best active compounds showed 91% tumor cell inhibition, whereas other three compounds showed more than 80% inhibition. Two-dimensional quantitative structure–activity relationship modeling and three-dimensional quantitative

  根据我们较早的工作，第450位N取代的2 N合成了-（取代的苯磺酰基）-L（+）谷氨酰胺，并筛选了其对癌细胞的抑制活性。最好的活性化合物显示出91％的肿瘤细胞抑制率，而其他三种化合物显示出80％以上的抑制率。进行了二维定量结构-活性关系建模和三维定量结构-活性关系k-近邻分子场分析研究，以深入了解结构要求，以进一步提高抗癌活性。考虑到这些化合物是谷氨酰胺酶的竞争性抑制剂，因此进行了分子对接研究，随后进行了分子动力学模拟分析。这项工作可能有助于开发新的抗癌药。
• Method for producing optical-active cis-piperidine derivatives
  申请人：——

  公开号：US20040171836A1

  公开（公告）日：2004-09-02

  An optical-active cis-piperidine derivative of high chemical purity and high optical purity is efficiently produced through optical resolution of a cis-piperidine derivative mixture, racemic cis-piperidine derivative with an optical-active tartaric acid derivative or an optical-active amino acid derivative. For the optical-active tartaric acid derivative, preferred are optical-active di(paratoluoyl)tartaric acid and optical-active di(4-methoxybenzoyl)tartaric acid; and for the optical-active amino acid derivative, preferred is optical-active N-benzenesulfonylphenylalanine.

  高化学纯度和高光学纯度的光学活性顺式哌啶衍生物可通过对顺式哌啶衍生物混合物进行光学分辨得到，所述混合物包括光学活性酒石酸衍生物或光学活性氨基酸衍生物与混合的顺式哌啶衍生物，所述混合的顺式哌啶衍生物为消旋的。对于光学活性酒石酸衍生物，首选的是光学活性二(对甲苯基)酒石酸和光学活性二(4-甲氧基苯甲酰)酒石酸；对于光学活性氨基酸衍生物，首选的是光学活性N-苯磺酰苯丙氨酸。
• NEW PROCESS FOR RESOLVING S-3- (AMINOMETHYL)-5-METHYLHEXANOIC ACID
  申请人：Xu Jiankang

  公开号：US20110098502A1

  公开（公告）日：2011-04-28

  The present invention relates to a process for resolving S-3-(Aminomethyl)-5-methylhexanoic acid, which adopts benzoyl-L-glutamic acid, 4-methyl benzoyl-L-glutamic acid, benzene sulfonyl-L-glutamic acid or 4-methyl benzene sulfonyl-L-glutamic acid as a resolution agent to make a first resolution to racemic 3-aminomethyl-5-methylhexanoic acid, and adopts the resolution agent same to that of the first resolution to make a second resolution to the first resolution product to obtain the second resolution product, thus the resolution salt product is obtained, and further hydrolyzed by an acid, the resolution agent is extracted to be separated, the pH is adjusted to be neutral, the product S-3-(Aminomethyl)-5-methylhexanoic acid, i.e. the pregabalin, is then precipitated by distillation, therefore the present invention has the characteristics of polluting the environment slightly, high efficiency and stability, simpleness and practicality, producing product with high purity and a low sproduction cost, and is suitable for large-scale production.

  本发明涉及一种用苯甲酰-L-谷氨酸、4-甲基苯甲酰-L-谷氨酸、苯磺酰-L-谷氨酸或4-甲基苯磺酰-L-谷氨酸作为分辨剂对拉氨酸的S-3-(氨甲基)-5-甲基己酸进行分辨的方法，对外消旋的3-氨甲基-5-甲基己酸进行第一次分辨，然后采用与第一次分辨相同的分辨剂对第一次分辨产物进行第二次分辨，得到第二次分辨产物，从而得到分辨盐产物，进一步通过酸水解，提取分辨剂进行分离，将pH值调节至中性，然后通过蒸馏使得S-3-(氨甲基)-5-甲基己酸即盐酸普瑞巴林沉淀，因此本发明具有污染环境轻微、高效稳定、简单实用、生产纯度高、生产成本低等特点，适用于大规模生产。