methyl ((2-nitrophenyl)sulfonyl)-L-leucinate | 215056-54-5

• 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 ((2-nitrophenyl)sulfonyl)-L-leucinate
• 英文别名: methyl (2S)-4-methyl-2-[(2-nitrophenyl)sulfonylamino]pentanoate
• CAS: 215056-54-5
• 化学式: C₁₃H₁₈N₂O₆S
• 分子量: 330.362
• InChiKey: COJXSYLDYLWOKY-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl ((2-nitrophenyl)sulfonyl)-L-leucinate 在 lithium hydroxide 、 potassium carbonate 、 巯基乙酸 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 methyl (2S)-2-[benzoyl(prop-2-enyl)amino]-4-methylpentanoate
  参考文献：
  名称：

  Microwave-accelerated cross-metathesis reactions of N-allyl amino acid substrates

  摘要：

  Microwave heating has been utilised for the cross-metathesis reaction of N-allyl amino acid substrates to generate olefin homodimers. Remarkable acceleration of the cross-metathesis reaction (minutes compared to hours) over conventional reflux heating was observed. In addition, improved reaction yields and similar E/Z ratios for the cross-metathesis products were achieved. (c) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2005.08.126
• 作为产物：
  描述：

  L-亮氨酸 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 methyl ((2-nitrophenyl)sulfonyl)-L-leucinate
  参考文献：
  名称：

  铑通过氧杂双环烯烃的不对称开环-内酯化级联催化铑催化对映选择性合成恶嗪酮。

  摘要：

  铑催化的氧杂双环烯烃的不对称开环反应是合成手性杂环的有效方法。我们证明手性催化剂与手性氨基酸衍生的前亲核试剂的成对组合导致非对映体羟基酯的立体发散合成。有利的构象偏好诱导一种非对映异构体随后的内酯​​化，从而导致恶二酮的高度对映选择性合成。

  DOI：

  10.1021/acs.orglett.9b02819

文献信息

• Cyclic phosphinamides and phosphonamides, novel series of potent matrix metalloproteinase inhibitors with antitumour activity
  作者：Morten Dahl Sørensen、Lars K.A. Blæhr、Mette K. Christensen、Thomas Høyer、Scilla Latini、Pernille-Julia V. Hjarnaa、Fredrik Björkling

  DOI：10.1016/j.bmc.2003.09.015

  日期：2003.12

  The design, synthesis, and structure-activity relationship (SAR) of a series of novel nonpeptidic cyclic phosphon- and phosphinamide-based hydroxamic acids as inhibitors of matrix metalloproteinases MMP-1, MMP-3, and MMP-9 are presented. Based on modelling studies and X-ray analysis, a model of the binding mode of these novel compounds in the MMP active site was obtained. This model provided a rational

  介绍了一系列新型非肽环状膦和次膦酰胺基异羟肟酸作为基质金属蛋白酶MMP-1，MMP-3和MMP-9的抑制剂的设计，合成和结构活性关系（SAR）。基于建模研究和X射线分析，获得了这些新型化合物在MMP活性位点的结合模式的模型。该模型为观察到的SAR数据提供了合理的解释，其中包括对不同的S1'定向取代基，锌络合基团，手性以及环状膦和次膦酰胺环的变化进行的系统研究。评价了四种化合物在人纤维肉瘤小鼠模型（HT1080）中的体内作用，并将其与参考化合物Prinomastat的体内作用进行了比较。对于所有四种化合物均观察到肿瘤生长的抑制。
• Modulating chitin synthesis in marine algae with iminosugars obtained by SmI₂ and FeCl₃-mediated diastereoselective carbonyl ene reaction
  作者：Marcel Holzwarth、Jan Ludwig、Alexander Bernz、Birgit Claasen、Asma Majoul、Julia Reuter、Anna Zens、Brigitte Pawletta、Ursula Bilitewski、Ingrid M. Weiss、Sabine Laschat

  DOI：10.1039/d2ob00907b

  日期：——

  were tested. For samarium diiodide we observed a superior stereoselectivity in comparison to iron(III) chloride and methylaluminium dichloride. To increase water solubility for testing and measurement of enzyme activity, the cyclization products were further functionalized. We established a novel biological chitin synthesis test system which allows quantitative investigation of chitin synthesis in the

  合成多羟基化哌啶如亚氨基糖的策略已受到广泛关注。已知这些物质与碳水化合物相关的酶、糖苷酶和糖基转移酶相互作用，几丁质合酶和纤维素合酶的大酶家族也属于这些酶。由于调节物质难以获得或价格昂贵，几丁质合酶的许多化学和生物学方面仍未探索。以对映体纯D-和L-氨基酸为出发点，通过路易斯酸催化的氨基酸衍生不饱和醛的环化反应制备了一系列亚氨基糖。因此，测试了不同的路易斯酸。对于二碘化钐，我们观察到与铁（III) 氯化物和甲基二氯化铝。为了增加水溶性以测试和测量酶活性，环化产物被进一步官能化。我们建立了一种新的生物几丁质合成测试系统，可以在光学显微镜下定量研究体内产生几丁质纤维的硅藻藻海藻中的几丁质合成。没有一种化合物表现出细胞毒性，但四种亚氨基糖中的两种增加了产生的几丁质纤维的长度。这是一个强有力的指标，表明这些化合物模拟了负责重新启动几丁质聚合的碳水化合物。
• Solid phase synthesis of enantiomerically pure polyhydroxyvalerolactams
  作者：Jordi Piró、Mario Rubiralta、Ernest Giralt、Anna Diez

  DOI：10.1016/s0040-4039(00)02146-8

  日期：2001.1

  A general method for the solid phase synthesis of type 2 3,4,5-trihydroxypiperidin-2-ones is described. Amination of D-ribonolactone 4 was accomplished using a Mitsunobu reaction, and type 7 aminolactone underwent direct lactamisation upon treatment with NaOAc. For the solid phase synthesis, the aminoacid was anchored directly to a TentaGel(R) resin, and the lactamisation step was concomitant with the cleavage from the resin. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Design, Synthesis, and Evaluation of Su- gar Amino Acid Based Inhibitors of Pro- tein Prenyl Transferases PFT and PGGT-1
  作者：Farid El Oualid、Brigitte E. A. Burm、Ingrid M. Leroy、Louis H. Cohen、Jacques H. van Boom、Hans van den Elst、Herman S. Overkleeft、Gijs A. van der Marel、Mark Overhand

  DOI：10.1021/jm049927q

  日期：2004.7.1

  Eleven analogues of the C-terminal Ca(1)a(2)X Motif found in natural substrates of the prenyl transferases PFT and PGGT-1 were synthesized and evaluated for their inhibition potency and selectivity against PFT and PGGT-1. Replacement of the central dipeptide part a(1)a(2) by a benzylated sugar amino acid resulted in a good and highly selective PFT inhibitor (8, IC50 = 250 +/- 20 nM). The methyl ester of 8 (13) selectively inhibited protein farnesylation in cultured cells.
• Microwave-accelerated cross-metathesis reactions of N-allyl amino acid substrates
  作者：Sally-Ann Poulsen、Laurent F. Bornaghi

  DOI：10.1016/j.tetlet.2005.08.126

  日期：2005.10

  Microwave heating has been utilised for the cross-metathesis reaction of N-allyl amino acid substrates to generate olefin homodimers. Remarkable acceleration of the cross-metathesis reaction (minutes compared to hours) over conventional reflux heating was observed. In addition, improved reaction yields and similar E/Z ratios for the cross-metathesis products were achieved. (c) 2005 Published by Elsevier Ltd.