(S)-3-amino-N-methoxy-N-methyl-succinamic acid tert-butyl ester | 109364-30-9

• 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: (S)-3-amino-N-methoxy-N-methyl-succinamic acid tert-butyl ester
• 英文别名: tert-butyl (3S)-3-amino-4-[methoxy(methyl)amino]-4-oxobutanoate
• CAS: 109364-30-9
• 化学式: C₁₀H₂₀N₂O₄
• 分子量: 232.28
• InChiKey: PRHQIRBTESAMIT-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  81.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-3-amino-N-methoxy-N-methyl-succinamic acid tert-butyl ester 在 lithium aluminium tetrahydride 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 生成 tert-butyl (3S)-3-[[(4S,7S)-7-benzamido-6,10-dioxo-2,3,4,7,8,9-hexahydro-1H-pyridazino[1,2-a]diazepine-4-carbonyl]amino]-4-oxobutanoate
  参考文献：
  名称：

  An efficient stereoselective synthesis of [3S(1S,9S)]-3-[[[9-(benzoylamino)octahydro-6,10-dioxo-6H-pyridazino-(1,2-a)(1,2)-diazepin-1-yl]-carbonyl]amino]-4-oxobutanoic acid, an interleukin converting enzyme (ICE) inhibitor

  摘要：

  The title compound 1 is a potent interleukin-1 beta-converting enzyme (ICE) inhibitor. Recently, an efficient chiral synthesis of compound 1 has been accomplished in our labs. The overall yield of this 18-step stereoselective synthesis was 9.8%. (C) 1999 Elsevier Science Ltd. Ail rights reserved.

  DOI：

  10.1016/s0960-894x(99)00236-x
• 作为产物：
  描述：

  N-苄氧羰基-L-天门冬氨酸 4-叔丁酯 在 palladium on activated charcoal N-甲基吗啉 、 氢气 作用下， 以 四氢呋喃 为溶剂， 生成 (S)-3-amino-N-methoxy-N-methyl-succinamic acid tert-butyl ester
  参考文献：
  名称：

  An efficient stereoselective synthesis of [3S(1S,9S)]-3-[[[9-(benzoylamino)octahydro-6,10-dioxo-6H-pyridazino-(1,2-a)(1,2)-diazepin-1-yl]-carbonyl]amino]-4-oxobutanoic acid, an interleukin converting enzyme (ICE) inhibitor

  摘要：

  The title compound 1 is a potent interleukin-1 beta-converting enzyme (ICE) inhibitor. Recently, an efficient chiral synthesis of compound 1 has been accomplished in our labs. The overall yield of this 18-step stereoselective synthesis was 9.8%. (C) 1999 Elsevier Science Ltd. Ail rights reserved.

  DOI：

  10.1016/s0960-894x(99)00236-x

文献信息

• Mild, Rapid, and Chemoselective Procedure for the Introduction of the 9-Phenyl-9-fluorenyl Protecting Group into Amines, Acids, Alcohols, Sulfonamides, Amides, and Thiols
  作者：Jacob Soley、Scott D. Taylor

  DOI：10.1021/acs.joc.9b02809

  日期：2020.2.21

  well as into alcohols and carboxylic acids, rapidly and in excellent yields, using 9-chloro-9-phenylfluorene (PhFCl)/N-methylmorpholine (NMM)/AgNO3. Nα-PhF-protected amino acids can be prepared from unprotected α-amino acids, rapidly and often in near quantitative yields, by treatment with N,O-bis(trimethylsilyl)acetamide (BSA) and then PhFCl/NMM/AgNO3. Primary alcohols can be protected with the PhF group

  9-苯基-9-芴基（PhF）基团已被用作氨基酸及其衍生物的Nα保护基团，这主要是由于其具有防止外消旋作用的能力。但是，使用标准协议安装该组，该协议使用9-溴-9-苯基芴/ K3PO4 / Pb（NO3）2，通常需要几天的时间，并且产量可能会有所不同。在这里，我们证明了使用9-氯-9-苯基芴基（PhFCl ）/ N-甲基吗啉（NMM）/ AgNO3。可以先用N，O-双（三甲基甲硅烷基）乙酰胺（BSA）然后用PhFCl / NMM / AgNO3处理，由未保护的α-氨基酸快速且经常以接近定量的收率制备Nα-PhF保护的氨基酸。在仲醇存在下，可以用PhF基团保护伯醇，且产率适中。使用PhFCl / AgNO3，可以在伯铵盐或羧酸的存在下以高收率保护伯醇。使用苯芴基醇（PhFOH）/ BF3·OEt2 / K3PO4可以以中等至良好的收率保护伯磺酰胺和酰胺，而使用PhFOH / BF3·OEt2则
• Arylsulfonamide ethers, and methods of use thereof
  申请人：——

  公开号：US20030096826A1

  公开（公告）日：2003-05-22

  Novel arylsulfonamide ether compounds and pharmaceutical compositions thereof are described. The use of the novel arylsulfonamide ether compounds and pharmaceutical compositions thereof as inhibitors of interleukin-1&bgr; converting enzyme and other cysteine proteases in the ICE family is also decribed. In addition, methods of treating stroke, inflammatory diseases, septic shock, repurfusion injury, Alzheimer's disease, and shigellosis using a compound of the invention or a pharmaceutical composition thereof are described.

  描述了新型芳基磺酰胺醚化合物及其药物组合物。还描述了将这些新型芳基磺酰胺醚化合物和药物组合物用作干扰素γ转化酶和其他ICE家族半胱氨酸蛋白酶的抑制剂的用途。此外，还描述了使用本发明的化合物或其药物组合物治疗中风、炎症性疾病、脓毒性休克、再灌注损伤、阿尔茨海默病和志贺氏菌病的方法。
• Isoxazoline derivative and a process for the preparation thereof
  申请人：LG Chem Investment Ltd.

  公开号：US06747050B1

  公开（公告）日：2004-06-08

  The present invention provides to an isoxazoline derivative of formula (I), the pharmaceutically acceptable salts, esters and stereochemically isomeric forms thereof, and the use of the derivative in inhibiting the activity of caspases. The present invention also provides a pharmaceutical composition for preventing inflammation and apoptosis which comprise the isoxazoline derivative, pharmaceutically acceptable salts, esters and stereochemically isomeric forms thereof and the process for preparing the same. The derivative according to the present invention can be effectively used in treating diseases due to caspases, such as, for example the disease in which cells are abnormally died, dementia, cerebral stroke, AIDS, diabetes, gastric ulcer, hepatic injury by hepatitis, sepsis, organ transplantation rejection reaction and anti-inflammation.

  本发明提供了一种式(I)的异噁唑啉衍生物，其药学上可接受的盐、酯和立体化异构体形式，以及该衍生物在抑制半胱天冬氨酸蛋白酶活性方面的用途。本发明还提供了一种用于预防炎症和细胞凋亡的药物组合物，包括异噁唑啉衍生物、药学上可接受的盐、酯和立体化异构体形式，以及其制备方法。根据本发明的衍生物可以有效用于治疗由半胱天冬氨酸蛋白酶引起的疾病，例如细胞异常死亡的疾病、痴呆症、脑卒中、艾滋病、糖尿病、胃溃疡、肝炎引起的肝损伤、败血症、器官移植排斥反应和抗炎症。
• Synthesis and biological activities of pseudopeptide analogs of the C-terminal heptapeptide of cholecystokinin. On the importance of the peptide bonds
  作者：Marc Rodriguez、Marie Francoise Lignon、Marie Christine Galas、Pierre Fulcrand、Christiane Mendre、Andre Aumelas、Jeanine Laur、Jean Martinez

  DOI：10.1021/jm00391a017

  日期：1987.8

  A series of pseudopeptide analogues of the C-terminal heptapeptide of cholecystokinin in which each peptide bond, one at a time, has been replaced by a CH2NH bond were synthesized: Z-Tyr(SO3-)-Nle-Gly-Trp-Nle-Asp psi-(CH2NH)Phe-NH2 (1), Z-Tyr(SO3-)-Nle-Gly-Trp-Nle psi (CH2NH)Asp-Phe-NH2 (2), Z-Tyr(SO3-)-Nle-Gly-Trp psi-(CH2NH)Nle-Asp-Phe-NH2 (3), Z-Tyr(SO3-)-Nle-Gly psi(CH2NH)Trp-Nle-Asp-Phe-NH2 (4)

  合成了胆囊收缩素C端七肽的一系列伪肽类似物，其中每个肽键一次被一个CH2NH键取代：Z-Tyr（SO3-）-Nle-Gly-Trp-Nle- Asp psi-（CH2NH）Phe-NH2（1），Z-Tyr（SO3-）-Nle-Gly-Trp-Nle psi（CH2NH）Asp-Phe-NH2（2），Z-Tyr（SO3-）-Nle -Gly-Trp psi-（CH2NH）Nle-Asp-Phe-NH2（3），Z-Tyr（SO3-）-Nle-Gly psi（CH2NH）Trp-Nle-Asp-Phe-NH2（4），Z- Tyr（SO3-）-Nle psi-（CH2NH）Gly-Trp-Nle-Asp-Phe-NH2（5），Z-Tyr（SO3-）-Met-Gly-Trp-Nle-Asp psi（CH2NH）Phe- NH2（6），Z-Tyr-（SO3-）-Met-Gly-Trp-Nle psi（
• Structure-based design of caspase-1 inhibitor containing a diphenyl ether sulfonamide
  作者：Aurash B Shahripour、Mark S Plummer、Elizabeth A Lunney、Tomi K Sawyer、Charles J Stankovic、Michael K Connolly、John R Rubin、Nigel P.C Walker、Kenneth D Brady、Hamish J Allen、Robert V Talanian、Winnie W Wong、Christine Humblet

  DOI：10.1016/s0960-894x(01)00573-x

  日期：2001.10

  A series of compounds was designed and prepared as inhibitors of interleukin-1 beta converting enzyme (ICE), also known as caspase-1. These inhibitors, which employ a diphenyl ether sulfonamide, were designed to improve potency by forming favorable interactions between the diphenyl ether rings and the prime side hydrophobic region. An X-ray crystal structure of a representative member of the diphenyl ether sulfonamide series bound to the active site of caspase-1 was obtained. (C) 2001 Elsevier Science Ltd. All rights reserved.