methyl (2S,4S)-4-azido-1-(p-tolylsulfonyl)pyrrolidine-2-carboxylate | 20275-13-2

• 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: methyl (2S,4S)-4-azido-1-(p-tolylsulfonyl)pyrrolidine-2-carboxylate
• 英文别名: (2S,4S)-methyl 4-azido-1-tosylpyrrolidine-2-carboxylate；N-tosyl-cis-4-azido-L-proline methyl ester；N-Tosyl-cis-4-azido-L-prolin-methylester；methyl (2S,4S)-4-azido-1-(4-methylphenyl)sulfonylpyrrolidine-2-carboxylate
• CAS: 20275-13-2
• 化学式: C₁₃H₁₆N₄O₄S
• 分子量: 324.36
• InChiKey: OEFSSCZFTLUDMS-JQWIXIFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  86.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl (2S,4S)-4-azido-1-(p-tolylsulfonyl)pyrrolidine-2-carboxylate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 生成 methyl (2S,4S)-4-amino-1-(p-tolylsulfonyl)pyrrolidine-2-carboxylate
  参考文献：
  名称：

  基质金属蛋白酶抑制剂α-磺酰基γ-（甘氨酰氨基）脯氨酸拟肽的设计，合成和初步评价

  摘要：

  设计，合成和测定了一系列新型的α-磺酰基γ-（甘氨酰氨基）脯氨酸拟肽衍生物，它们对基质金属蛋白酶-2（MMP-2），氨基肽酶N（APN）/ CD13和HDAC的活性。结果表明，与APN和HDAC相比，所有化合物均显示出对MMP-2的高度选择性抑制。还研究了某些化合物对SKOV3，HL60和A549细胞的抗增殖活性。与对照LY52相比，在酶促抑制分析和基于细胞的分析中均具有优异活性的化合物12u可用作进一步开发MMP抑制剂的先导化合物。

  DOI：

  10.1016/j.bmc.2013.12.025
• 作为产物：
  描述：

  N-tosyl-trans-4-hydroxy-L-proline 在 sodium azide 作用下， 以 乙醚 为溶剂， 生成 methyl (2S,4S)-4-azido-1-(p-tolylsulfonyl)pyrrolidine-2-carboxylate
  参考文献：
  名称：

  Trans-4-aminoproline, a phytotoxic metabolite with herbicidal activity produced by Ascochyta caulina

  摘要：

  A phytotoxic metabolite, characterized through NMR techniques and synthetic methods as trans-4-aminoproline, was isolated from the culture filtrates of Ascochyta caulina, a promising mycoherbicide for biological control of Chenopodium album. The metabolite, which shows interesting phytotoxic properties, together with ascaulitoxin (recently characterized as N-2-beta-D-glucoside of the unusual bis-amino acid 2,4,7-triamino-5-hydroxyoctandioc acid) and another unidentified compound, compose an active fraction of A. caulina culture filtrates with promising herbicidal properties. When assayed on leaves of host and non host dicots, including wild and cultivated plants, the trans-4-aminoproline showed a wide range of toxicity, with leaves of C. album being the most sensitive. Other interesting aspects were its inefficacy on several monocots, both cultivated and wild and its lack of antifungal, antibiotic and zootoxic activities. This is the first report on trans-4-aminoproline as naturally occurring compound and phytotoxic metabolite produced by A. caulina. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(99)00507-5

文献信息

• Azido, imido, amido and amino derivatives of mercaptoacyl prolines and pipecolic acids having hypotensive activity
  申请人：E.R. Squibb & Sons, Inc.

  公开号：EP0042639A2

  公开（公告）日：1981-12-30

  Azido, imido, amido and amino derivatives of mercap- toacyl prolines and pipecolic acids having the formula wherein -NR1-R2 is azido or R1 and R2 are the same or different and are hydrogen, alkyl, cycloalkyl, 1-adamantyl, aryl, arylalkyl, alkylcarbonyl, arylcarbonyl, arylalkylcarbonyl, alkylsulfonyl, arylsulfonyl, or arylvinylcarbonyl, or together with the nitrogen atom to which they are attached R, and R2 are 1-pyrrolidinyl, 1-piperidinyl, 1-homopiperidinyl, 4-morpholinyl, 4-alkyl-1-piperazinyl, 4-aryl-1-piperazinyl, 1-imidazolyl, 1-pyrrolidinyl-2,5-dione, 3-alkyl-1-pyrrolidinyl-2,5-dione, 3-aryl-1-pyrrolidinyl-2,5-dione, 1-piperidinyl-2,6-dione,3-alkyl-1- piperidinyl-2,6-dione, 3-aryl-1-piperidinyl,2-6-dione, 2H-isoindol-2-yl-1,3-dione, hexahydro-2H-isoindol-2-yl-1,3-dione, 2,5-dihydro-2,5-dioxo-lH-pyrrol-1-yl, 1,1,3- trioxo-1,2-benzisothiazol-2(3H)-yl, or 1,3-dihydro-1,3-dioxo-2H-benz[de]isoquinolin-2-yl; R3 is hydrogen, alkyl, aryl, arylalkyl, or a hydrolyzable acyl protecting group; R4 is hydrogen, alkyl, alkylthio, or trifluoromethyl; Rs is hydrogen, alkyl, or arylalkyl; n is 0, 1 or 2; and p is 1 or 2; or a salt thereof, or symmetrical dimer thereof are useful for the treatment of hypertension.

  巯基脯氨酸和哌啶醇酸的叠氮、亚胺、酰胺和氨基衍生物，其式为 其中 -NR1-R2 为叠氮基，或 R1 和 R2 相同或不同，且为氢、烷基、环烷基、1-金刚烷基、芳基、芳烷基、烷基羰基、芳基羰基、芳基烷基羰基、烷基磺酰基、芳基磺酰基、芳基乙烯基羰基或芳基乙烯基羰基、或芳基乙烯基羰基，或连同所连接的氮原子 R 和 R2 是 1-吡咯烷基、1-哌啶基、1-高哌啶基、4-吗啉基、4-烷基-1-哌嗪基、4-芳基-1-哌嗪基1-咪唑基、1-吡咯烷基-2,5-二酮、3-烷基-1-吡咯烷基-2,5-二酮、3-芳基-1-吡咯烷基-2,5-二酮、1-哌啶基-2,6-二酮、3-烷基-1-哌啶基-2,6-二酮、3-芳基-1-哌啶基 2-6-二酮、2H-isoindol-2-yl-1,3-dione, hexahydro-2H-isoindol-2-yl-1,3-dione, 2,5-dihydro-2,5-dioxo-lH-pyrrol-1-yl, 1,1,3- trioxo-1,2-benzisothiazol-2(3H)-yl, or 1,3-dihydro-1,3-dioxo-2H-benz[de]isoquinolin-2-yl; R3 是氢、烷基、芳基、芳烷基或可水解的酰基保护基团； R4 是氢、烷基、烷硫基或三氟甲基； Rs 是氢、烷基或芳烷基； n 是 0、1 或 2；以及 p 为 1 或 2； 或其盐，或其对称二聚体可用于治疗高血压。
• Regioselective Synthesis and Slow-Release Suzuki–Miyaura Cross-Coupling of MIDA Boronate-Functionalized Isoxazoles and Triazoles
  作者：Jonathan E. Grob、Jill Nunez、Michael A. Dechantsreiter、Lawrence G. Hamann

  DOI：10.1021/jo201973t

  日期：2011.12.16

  The efficient preparation of heterocycles with a range of substitutions ortho to heteroatoms remains as a challenge in organic synthesis, particularly relevant to the construction of druglike molecules due to the ubiquitous presence of such moieties in that chemical space. Modular installation of heterocyclic building blocks using Suzuki-Miyaura cross-coupling is a conceptually useful strategy to address this challenge, though this has historically been met with technical difficulty due to issues of inaccessibility and instability of the requisite heterocyclic boronates. Herein we report a mild and highly regioselective cycloaddition approach which affords convenient access to stable MLDA boronate-functionalized isoxazoles and triazoles and their subsequent efficient Suzuki-Miyaura cross-coupling. This methodology is then further applied to a set of druglike compounds in an efficient one-pot telescoped sequence in line with green chemistry principles.
• KRAPCHO, J.;WADE, P. C.
  作者：KRAPCHO, J.、WADE, P. C.

  DOI：——

  日期：——
• US4310461A
  申请人：——

  公开号：US4310461A

  公开（公告）日：1982-01-12
• US4497953A
  申请人：——

  公开号：US4497953A

  公开（公告）日：1985-02-05