N-phthalimide-L-leucinyl chloride | 3183-10-6

• 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
• 英文名称: N-phthalimide-L-leucinyl chloride
• 英文别名: N-phthaloyl-(S)-leucyl chloride；(2S)-2-(1,3-dioxoisoindol-2-yl)-4-methylpentanoyl chloride
• CAS: 3183-10-6
• 化学式: C₁₄H₁₄ClNO₃
• 分子量: 279.723
• InChiKey: MDULUARQXVRLRT-NSHDSACASA-N

物化性质

• 沸点：
  379.5±25.0 °C(Predicted)
• 密度：
  1.312±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  54.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-phthalimide-L-leucinyl chloride 在 Pd-BaSO₄ 盐酸 、 氢气 、 zinc(II) iodide 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 xylene 为溶剂， 反应 67.5h， 生成 (2R,3S)-3-amino-2-hydroxy-5-methylhexanoic acid
  参考文献：
  名称：

  Renin inhibitors. Substitution of the leucyl residues of Leu-Leu-Val-Phe-OCH3 with 3-amino-2-hydroxy-5-methylhexanoic acid

  摘要：

  The 2S,3S and 2R,3S diastereoisomers of the hydroxy amino acid 3-amino-2-hydroxy-5-methylhexanoic acid (AHMHA) were synthesized and substituted for the leucyl residues of Leu-Leu-Val-Phe-OCH3 to yield the following analogues: AHMHA-Leu-Val-Phe-OCH3, AHMHA-Val-Phe-OCH3, and Leu-AHMHA-Val-Phe-OCH3. These analogues were tested in vitro for their ability to inhibit human amniotic renin. All of the analogues were found to inhibit renin to some extent with inhibitory constants in the range of 10(-3) to 10(-4) M. The analogues AHMHA-Leu-Val-Phe-OCH3 and AHMHA-Val-Phe-OCH3 exhibited competitive inhibition when the 2S,3S isomer of AHMHA was employed and noncompetitive kinetics when the 2R,3S isomer of AHMHA was used. For the Leu-AHMHA-Val-Phe-OCH3 analogues, competitive kinetics were observed regardless of the isomer of AHMHA employed. These latter analogues also proved to be the most active in the above series.

  DOI：

  10.1021/jm00347a024
• 作为产物：
  描述：

  L-亮氨酸 在 氯化亚砜 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 4.0h， 生成 N-phthalimide-L-leucinyl chloride
  参考文献：
  名称：

  Synthesis of novel phthalimido oxime pseudoesters and evaluation of their cytotoxicity

  摘要：

  在三乙胺和二氯甲烷存在下，于 0.C 下通过替代酮肟与各种 N-取代?-氨基酸氯化物反应合成了一系列新型光学纯肟伪酯衍生物，并通过红外和 1D-NMR 方法对其结构进行了表征。对合成的化合物进行了抑制人结肠癌细胞和人上皮细胞增殖能力的测试。结果表明，其中一些化合物具有显著的细胞毒性作用。

  DOI：

  10.2298/jsc180302082m

文献信息

• Synthesis of enantiomers of 3-methyl- and 3-phenyl-3,4-dihydro-2H-[1,4]benzothiazines and their 1,1-dioxides via an acylative kinetic resolution protocol
  作者：Dmitry A. Gruzdev、Evgeny N. Chulakov、Liliya Sh. Sadretdinova、Mikhail I. Kodess、Galina L. Levit、Victor P. Krasnov

  DOI：10.1016/j.tetasy.2015.01.010

  日期：2015.2

  (ee >97%). This method proved to be less suitable for the preparation of the (S)-enantiomer of 3,4-dihydro-3-phenyl-2H-[1,4]benzothiazine (ee up to 93%) and its sulfone (ee 82%) which were both obtained in low yields. The loss of enantioselectivity for (S)-3,4-dihydro-3-phenyl-2H-[1,4]benzothiazine and its sulfone occurred during hydrolysis of the corresponding diastereoisomerically pure amides.

  已经发现，（的酰氯小号） -萘普生，Ñ -phthaloyl-（小号） -亮氨酸，和Ñ甲苯磺酰基（小号） -脯氨酸是外消旋的3-甲基的acylative动力学拆分高效手性拆分试剂和3-苯基-3,4-二氢-3-甲基-2 ħ - [1,4]苯并噻嗪。基于该实验结果，包括acylative动力学拆分制备性协议，随后通过单个（主）非对映体酰胺和酰胺键的随后水解分离，提出了。使用与各种手性拆分剂该方法中，（小号） -和（- [R）3,4-二氢-3-甲基-2 -对映体ħ-得到[1,4]苯并噻嗪（EE> 99％）。酰胺的非对映体相应的氧化，随后导致了（脱酰小号） -和（- [R ）-对映体的3,4-二氢-3-甲基-2 ħ - [1,4]苯并噻嗪1,1-二氧化钛（ee值> 97％）。这种方法被证明是不适合的（制备小号）3,4-二氢-3-苯基-2 -对映体ħ - [1,4]苯并噻嗪（EE高达93％）和它的砜（EE
• Synthesis and biological activity of (3,5-disubstituted-1<i>H</i>-1,2,4-triazol-1-yl)benzophenone derivatives
  作者：Kentaro Hirai、Hirohiko Sugimoto、Teruyuki Ishiba、Toshio Fujishita、Yuji Tsukinoki、Katsumi Hirose

  DOI：10.1002/jhet.5570190621

  日期：1982.11

  The synthesis of (5-acylaminomethyl-3-carbamoyl-1H-1,2,4-triazol-1-yl)benzophenone derivatives 4a-i, 14a-d, 15a-d, 16a-c, is described. Acylation of the key intermediate, 1-benzoylphenylazo-1-aminoacetamide 7, followed by cyclization in the presence of acid afforded 1H-1,2,4-triazole derivatives. These compounds were evaluated for their central nervous system (CNS) activity. Some of these compounds

  描述了（5-酰基氨基甲基-3-氨基甲酰基-1 H -1,2,4-三唑-1-基）二苯甲酮衍生物4a-i，14a-d，15a-d，16a-c的合成。关键中间体1-苯甲酰基苯基偶氮-1-氨基乙酰胺7的酰化，然后在酸存在下环化，得到1 H -1,2,4-三唑衍生物。对这些化合物的中枢神经系统（CNS）活性进行了评估。当口服时，这些化合物中的一些在小鼠抗戊烯四唑和旋转脚架试验中表现出高活性。
• Trifluoroborane-Catalyzed C–H Functionalization/S–H Insertion Reaction: Construction of N,S-Acetal Quaternary Centers
  作者：Yan Cai、Haihong Ge、Weize Sun、Zhiwei Miao

  DOI：10.1055/s-0034-1380384

  日期：2015.6

  The trifluoroborane-catalyzed C–H functionalization/S–H insertion reaction of α-diazophosphonates with thiols has been developed. A plausible reaction mechanism has been proposed to understand the combined reaction. This process provides straightforward access to N,S-acetals containing quaternary centers in moderate to good yields and chemoselectivity.

  三氟硼烷催化的α-重氮磷酸酯与硫醇的C-H官能化/S-H插入反应已经被开发出来。已经提出了一个合理的反应机理来理解这个复合反应。这个过程以中等到良好的产率和化学选择性提供了直接访问含有季铵中心的N,S-缩醛。
• Huperzine a prodrugs and uses thereof
  申请人：Pan Bai-Chuan

  公开号：US20070082922A1

  公开（公告）日：2007-04-12

  Disclosed are huperzine A prodrugs and method of synthesis thereof. The invention further relates to methods of treating, preventing or reversing neurodegenerative diseases, such as, Alzheimer's Disease and neuronal dysfunctions, such as, memory impairment using a pharmaceutical composition comprising a huperzine A prodrug as disclosed herein.

  揭示了Huperzine A 前药及其合成方法。本发明还涉及使用包含本文所述的 Huperzine A 前药的药物组合物治疗、预防或逆转神经退行性疾病，如阿尔茨海默病和神经功能障碍，如记忆障碍的方法。
• [EN] SMALL MOLECULES AGAINST CEREBLON TO ENHANCE EFFECTOR T CELL FUNCTION<br/>[FR] PETITES MOLÉCULES DIRIGÉES CONTRE LE CÉRÉBLON POUR AMÉLIORER LA FONCTION DES LYMPHOCYTES T EFFECTEURS
  申请人：H LEE MOFFITT CANCER CENTER & RES INST INC

  公开号：WO2017161119A1

  公开（公告）日：2017-09-21

  Disclosed are small molecules against cereblon to enhance effector T cell function. Methodos of making thes molecules and methods of using them to treat various disease states are also disclosed.

  披露了针对小脑蛋白以增强效应T细胞功能的小分子。还披露了制造这些分子的方法以及使用它们治疗各种疾病状态的方法。