N^α-Boc-Ile-OBt | 83690-54-4

• 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^α-Boc-Ile-OBt
• 英文别名: Boc-Ile-OBt；benzotriazol-1-yl (2S,3S)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate
• CAS: 83690-54-4
• 化学式: C₁₇H₂₄N₄O₄
• 分子量: 348.402
• InChiKey: SSYKOVYIIYLOAQ-FZMZJTMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.33
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  95.34
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  N^α-Boc-Ile-OBt 在 N-甲基吗啉 、 盐酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 乙酸乙酯 为溶剂， 反应 24.5h， 生成 1-(2-amino-3-methylpentanoyl)-4-hydroxypyrrolidine-2-carboxylic acid
  参考文献：
  名称：

  Design, synthesis, inhibitory activity, and SAR studies of pyrrolidine derivatives as neuraminidase inhibitors

  摘要：

  A series of pyrrolidine derivatives were synthesized and evaluated for their ability to inhibit neuraminidase (NA) of influenza A virus (H3N2). All compounds were synthesized in good yields starting from commercially 4-hydroXy-L-proline using a suitable synthetic strategy. These compounds showed potent inhibitory activity against influenza A neuraminidase. Within this series, five compounds, 6e, 9c, 9e, 9f, and 10e, have good potency (IC50 = 1.56-2.71 mu M) which are compared to that the NA inhibitor Oseltarnivir (IC50 = 1.06 mu M), and could be used as lead compoundS in the future. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.01.020
• 作为产物：
  描述：

  BOC-L-异亮氨酸 、 1-羟基苯并三唑 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.08h， 生成 N^α-Boc-Ile-OBt
  参考文献：
  名称：

  未修饰肽与 5-18F-(三氟甲基)二苯并噻吩三氟甲磺酸盐的 18F-三氟甲基化

  摘要：

  5-(三氟甲基)-二苯并噻吩三氟甲磺酸盐的 18F 标记，通常称为 Umemoto 试剂，已通过卤素交换 18F-氟化与 18F-氟化物，然后与 Oxone 和三氟甲磺酸酐氧化环化来完成。这种新的 18F 试剂允许在硫醇半胱氨酸残基处对未修饰的肽进行直接化学选择性 18F 标记。

  DOI：

  10.1021/jacs.7b10227

文献信息

• (3S)-N-(l-Aminoacyl)-1,2,3,4-tetrahydroisoquinolines, a class of novel antithrombotic agents: Synthesis, bioassay, 3D QSAR, and ADME analysis
  作者：Meiqing Zheng、Xiaoyi Zhang、Ming Zhao、Heng Wei Chang、Wei Wang、Yuji Wang、Shiqi Peng

  DOI：10.1016/j.bmc.2008.09.019

  日期：2008.11

  To increase antithrombotic activity, 3S-tetrahydroisoquinoline-3-carboxylic acid (1) was modified with natural amino acids to form 19 novel dipeptide analogs, 3S-tetrahydroisoquinoline-3-carboxyamino acids (5a-s), targeting the intestinal peptide transport system. In vitro assay of 5a-s indicated that their potencies for inhibiting adenosine diphosphate (ADP), arachidonic acid (AA), platelet-activating factor (PAF), and thrombin (TH)-induced platelet aggregations were higher than that of 1. Additionally, in vivo assay of 5a-s indicated that their potencies for inhibiting thrombogenesis in rats were also higher than that of 1. Among the candidates, 5h with Ser attachment showed the most impressive features for further development. According to molecular field analysis based Cerius(2) QSAR module, two equations (r, 0.961 and 0.988) correlating the structures with both in vitro and in vivo activities of 5a-s were established. ADMET calculations predict higher intestinal absorption for compounds 5a-s. Further investigation with 5h as a lead compound is underway. (C) 2008 Elsevier Ltd. All rights reserved.
• Lyakhov; Suveyzdis; Litvinova, Pharmazie, 2000, vol. 55, # 10, p. 733 - 736
  作者：Lyakhov、Suveyzdis、Litvinova、Andronati、Rybalko、Dyadyun

  DOI：——

  日期：——
• Polymer-Assisted solution-Phase (PASP) parallel synthesis of an α-Ketothiazole library as tissue factor VIIa inhibitors
  作者：Michael S South、Thomas A Dice、Thomas J Girard、Rhonda M Lachance、Anna M Stevens、Roderick A Stegeman、William C Stallings、Ravi G Kurumbail、John J Parlow

  DOI：10.1016/s0960-894x(03)00398-6

  日期：2003.7

  A solution-phase synthesis of an alpha-ketothiazole library of the general form D-Phe-L-AA-L-Arg-alpha-ketothiazole is described. The five-step synthesis is accomplished using a combination of polymeric reagents and polymer-assisted solution-phase purification protocols, including reactant-sequestering resins, reagent-sequestering resins, and tagged reagents. The multi-step synthesis affords the desired alpha-ketothiazole products in excellent purities and yields. A variety Of L-amino acid inputs were used to probe the S2 pocket of the tissue factor (TF) Vila enzyme to influence both potency and selectivity. An X-ray crystal structure of compound 10e bound to the TF/VIIa complex was obtained that explains the observed selectivity. The alpha-ketothiazoles were found to be potent, reversible-covalent inhibitors of tissue factor VIIa, with some analogues demonstrating selectivity versus thrombin. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Design and synthesis of highly potent and selective cyclic dynorphin A analogs. 2. New analogs
  作者：Andrew M. Kawasaki、Richard J. Knapp、Thomas H. Kramer、Amanda Walton、William S. Wire、Shinicki Hashimoto、Henry I. Yamamura、Frank Porreca、Thomas F. Burks、Victor J. Hruby

  DOI：10.1021/jm00058a012

  日期：1993.3

  We have designed and synthesized several cyclic disulfide-containing peptide analogs of dynorphin A (Dyn A) which are conformationally constrained in the putative ''address' segment of the opioid ligand. Several of these Dyn A analogs exhibit unexpected apparent selectivities for the kappa and mu opioid receptors(s) of the central vs peripheral nervous systems. Thus, incorporation of conformational constraint in the putative ''address'' segment of Dyn A analogs has resulted in the kappa/mu opioid receptor ligands [L-Pen5,Cys11]Dyn A1-11-NH2 (4), [Cys5,Cys10]Dyn A1-11-NH2 (5), [Cys5,Cys9]DynA1-11-NH2(6), and [Cys4,Cys9,Arg10]DynA1-11-NH2(7). All of these analogs possess high kappa and mu opioid receptor affinities for the central receptor (guinea pig brain), but effect only weak potency at peripheral kappa and mu opioid receptors (GPI). In fact cyclic dynorphin A analog 4 shows >19 000-fold differences between central kappa opioid affinity and potency in the guinea pig ileum (GPI). Additionally analog 4 is not an antagonist in the GPI, suggesting possible receptor differences between these sites. Substitution of Tyr1 by Phe1 in the cyclic 1-11 series gave the analog [Phe1,Cys5,Cys11]Dyn A1-11-NH2 (1) that was surprisingly potent in the guinea pig brain binding assay (IC50 = 15.1 nM) at the kappa receptor, but was inactive in the GPI and mouse vas deferens bioassays. D-Ala2 and TiC4 analogs of 1 had lower affinity at brain kappa receptors and had very weak potencies in the GPI and MVD bioassays. On the other hand, [Cys6,Cys10]DynA1-11-NH2 (8), [Cys8,D-Cys13]DynA1-13-NH2 (9), [D-CyS8,D-CyS12 ]DynA1-13-NH2 (10), and [D-Pro10,Cys5, Cys13]-Dyn Al-13-NH2 (11) were surprisingly potent in the GPI bioassay, though considerable apparent selectivity for central receptors is still retained. The apparent lack of correlation between the pharmacological profiles observed in smooth muscle and in the brain binding assays, particularly with 1 and 4, may suggest the existence of different subtypes of the kappa and mu opioid receptors in the brain and peripheral systems.
• Krchnak, Viktor; Vagner, Josef; Hirsch, Ivan, Collection of Czechoslovak Chemical Communications, 1988, vol. 53, # 11A, p. 2645 - 2653
  作者：Krchnak, Viktor、Vagner, Josef、Hirsch, Ivan

  DOI：——

  日期：——