N`-叔丁氧羰基-L-赖氨酰胺盐酸盐 | 112803-72-2

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 赖氨酸类衍生物
• 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
• 中文名称: N`-叔丁氧羰基-L-赖氨酰胺盐酸盐
• 中文别名: (S)-叔丁基(5,6-二氨基-6-氧代己基)氨基甲酸盐酸盐；N’-叔丁氧羰基-L-赖氨酰胺盐酸盐；NΕ叔丁氧羰酰基赖氨酸酰氨盐酸盐；-叔丁氧羰基-L-赖氨酰胺盐酸盐；N'-叔丁氧羰基-L-赖氨酰胺盐酸盐；N-叔丁氧羰基-L-赖氨酰胺盐酸盐；H-Lys(Boc)-NH2
• 英文名称: H-Lys(Boc)-NH2 hydrochloride
• 英文别名: N(ε)-t-Boc-L-lysineamide hydrochloride；H-Lys(Boc)-NH2*HCl；N-ε-tert-butoxycarbonyl-L-lysine amide hydrochloride；N^ε-Boc-L-lysinamide hydrochloride；H-Lys(boc)-NH2 hcl；tert-butyl N-[(5S)-5,6-diamino-6-oxohexyl]carbamate;hydrochloride
• CAS: 112803-72-2
• 化学式: C₁₁H₂₃N₃O₃*ClH
• 分子量: 281.783
• InChiKey: BVWRJFHMGKKDQR-QRPNPIFTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.92
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N`-叔丁氧羰基-L-赖氨酰胺盐酸盐 在 三聚氟氰 、 TEA 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 、 sodium iodide 作用下， 以 二甲基亚砜 、 丙酮 为溶剂， 反应 2.0h， 生成 (2S)-2-[[2-[fluoro(methoxy)phosphoryl]acetyl]amino]-6-(pyren-1-ylsulfonylamino)hexanamide
  参考文献：
  名称：

  合成针对乙酰胆碱酯酶活性位点的荧光探针。

  摘要：

  制备了六个与荧光团相连的有机磷化合物，以选择性地修饰乙酰胆碱酯酶的活性位点并将探针递送至峡谷区域。发现根据亚甲基（CH2）基团的长度而变化的两种化合物pyr-SO2NH（CH2）nNHC（O）CH2CH2P（O）（OEt）（F）（其中n = 2或3）是有效的，不可逆的重组小鼠AChE的抑制剂（Ki约为10（5）M（-1）min（-1））。尺寸排阻色谱法得到荧光标记的胆碱酯酶缀合物。

  DOI：

  10.1016/s0960-894x(00)00275-4

文献信息

• [EN] PYRIDINE COMPOUNDS AS SODIUM CHANNEL BLOCKERS<br/>[FR] COMPOSÉS PYRIDINES COMME BLOQUEURS DES CANAUX SODIQUES
  申请人：PURDUE PHARMA LP

  公开号：WO2012007836A1

  公开（公告）日：2012-01-19

  The invention relates to substituted pyridine compounds of Formula I: (I) or a pharmaceutically acceptable salt, prodrug, or solvate thereof, wherein A1, X, A2, R1a, R1b, R1c, G, and z are defined as set forth in the specification. The invention is also directed to the use of compounds of Formula I to treat a disorder responsive to the blockade of sodium channels. Compounds of the present invention are especially useful for treating pain.

  该发明涉及公式I的取代吡啶化合物：(I)或其药学上可接受的盐、前药或溶剂化合物，其中A1、X、A2、R1a、R1b、R1c、G和z的定义如规范中所述。该发明还涉及利用公式I的化合物治疗对钠通道阻滞有响应的疾病。本发明的化合物特别适用于治疗疼痛。
• 2-(Guanidiniocarbonyl)furans as a New Class of Potential Anion Hosts: Synthesis and First Binding Studies
  作者：Carsten Schmuck、Uwe Machon

  DOI：10.1002/ejoc.200600324

  日期：2006.10

  The synthesis of a new class of potential anion hosts, the 2-(guanidiniocarbonyl)furans 5a–d, is presented in this study. The facile decomposition of furans under acidic conditions makes the synthesis of these compounds challenging. First binding studies showed that the (guanidiniocarbonyl)furans are much more acidic (pKa ≈ 5.5) than the analogous pyrroles (pKa ≈ 7) previously introduced by us for

  本研究介绍了一类新的潜在阴离子宿主 2-（胍基羰基）呋喃 5a-d 的合成。呋喃在酸性条件下的容易分解使得这些化合物的合成具有挑战性。第一次结合研究表明，（胍基羰基）呋喃比我们之前引入的用于在水性溶剂中结合氧阴离子的类似吡咯（pKa ≈ 7）酸性更强（pKa ≈ 5.5）。因此，阴离子与呋喃衍生物的结合仅在低于 pH = 5 的酸性溶液中发生。因此，羧酸盐不能有效结合，而例如，碱性较弱的硫酸氢盐与 5b 结合，结合常数为 K = 600 M– 1 在含水 DMSO 中，即使存在大量过量的缓冲液。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
• Chiral recognition mechanism studies of Tyr‐Arg‐Phe‐Lys‐NH₂ tetrapeptide on crown ether‐based chiral stationary phase
  作者：Toms Upmanis、Eduards Sevostjanovs、Helena Kažoka

  DOI：10.1002/chir.23619

  日期：2024.1

  between llll/dddd enantiomers of Tyr-Arg-Phe-Lys-NH2 and crown ether selectors. Enantioselective proton shifts were observed in studied tetrapeptide tyrosine and phenylalanine residues exclusively for llll enantiomer upon binding with S-(3,3′-diphenyl-1,1′-binaphthyl)-20-crown-6 selector (and dddd enantiomer with R-(3,3′-diphenyl-1,1′-binaphthyl)-20-crown-6 selector), indicating that these two amino acid

  尽管冠醚 CSP 的手性识别已被普遍理解，但在分子水平上，拆分的确切机制仍不清楚。此外，短肽分析物通常含有多个能够与冠醚选择器结合的氨基部分。为了扩展对手性识别机制的理解，Tyr-Arg-Phe-Lys-NH 2四肽III/dddd对映体在S - 和R -(3,3'-二苯基-1,1'-上的极性有机模式分离使用 50 mM 高氯酸的甲醇溶液作为流动相，对联萘)-20-crown-6 固定相进行了研究。对四肽对映体和冠醚选择剂之间形成的复合物进行质谱分析，证实了与普遍可接受的 1:1 化学计量的偏差，显示加合物具有 1:1、1:2 和 1:3 化学计量。通过NMR对络合诱导的位移的进一步研究表明Tyr-Arg-Phe-Lys-NH 2的III/dddd对映体与冠醚选择剂之间的不同结合机制。在所研究的四肽酪氨酸和苯丙氨酸残基中观察到在与S- (3,3'-二苯基-1,1'-联萘基)-20-crow
• Design, Synthesis, and Structure−Activity Relationships of Macrocyclic Hydroxamic Acids That Inhibit Tumor Necrosis Factor α Release in Vitro and in Vivo
  作者：Chu-Biao Xue、Matthew E. Voss、David J. Nelson、James J.-W. Duan、Robert J. Cherney、Irina C. Jacobson、Xiaohua He、John Roderick、Lihua Chen、Ronald L. Corbett、Li Wang、Dayton T. Meyer、Kenneth Kennedy、William F. DeGrado、Karl D. Hardman、Christopher A. Teleha、Bruce D. Jaffee、Rui-Qin Liu、Robert A. Copeland、Maryanne B. Covington、David D. Christ、James M. Trzaskos、Robert C. Newton、Ronald L. Magolda、Ruth R. Wexler、Carl P. Decicco

  DOI：10.1021/jm010127e

  日期：2001.8.1

  To search for TNF-alpha (tumor necrosis factor alpha) converting enzyme (TACE) inhibitors, we designed a new class of macrocyclic hydroxamic acids by linking the PI and P2 ' residues of acyclic anti-succinate-based hydroxamic acids. A variety of residues including amide, carbamate, alkyl, sulfonamido, Boc-amino, and amino were found to be suitable P1-P2 ' linkers. With an N-methylamide at P3 ', the 13-16-membered macrocycles prepared exhibited low micromolar activities in the inhibition of TNF-alpha release from LPS-stimulated human whole blood. Further elaboration in the P3 ' -P4 ' area using the cyclophane and cyclic carbamate templates led to the identification of a number of potent analogues with IC50 values of less than or equal to 0.2 muM in whole blood assay (WBA). Although the P3 ' area can accommodate a broad array of structurally diversified functional groups including polar residues, hydrophobic residues, and amino and carboxylic acid moieties, in both the cyclophane series and the cyclic carbamate series, a glycine residue at P3 ' was identified as a critical structural component to achieve both good in vitro potency and good oral activity. With a glycine residue at P3 ', an N-methylamide at P4 ' provided the best cyclophane analogue, SL422 (WBA IC50 = 0.22 muM, LPS-mouse ED50 = 15 mg/kg, po), whereas a morpholinylamide at P4 ' afforded the most potent and most orally active cyclic carbamate analogue, SP057 (WBA IC50 = 0.067 muM, LPS-mouse ED50 = 2.3 mg/kg, po). Further profiling for SL422 and SP057 showed that these macrocyclic compounds are potent TACE inhibitors, with K-i values of 12 and 4.2 nM in the porcine TACE assay, and are broad-spectrum MMP inhibitors. Pharmacokinetic studies in beagle dogs revealed that SL422 and SP057 are orally bioavailable, with oral bioavailabilities of 11% and 23%, respectively.
• Antitumor Imidazotetrazines. 41. Conjugation of the Antitumor Agents Mitozolomide and Temozolomide to Peptides and Lexitropsins Bearing DNA Major and Minor Groove-Binding Structural Motifs
  作者：Jill Arrowsmith、Sharon A. Jennings、Alan S. Clark、Malcolm F. G. Stevens

  DOI：10.1021/jm020936d

  日期：2002.12.1

  Carboxylic acids derived from the amido groups of the antitumor agents mitozolomide and temozolomide have been conjugated to simple amino acids and peptides by carbodiimide coupling. Solid-state peptide synthesis has been applied to link the acids to DNA major groove-binding peptidic motifs known to adopt alpha-helical conformations. Attachment of the acids to pyrrole and imidazole polyamidic lexitropsins gave a series of potential DNA minor groove- binding ligands. In vitro biological evaluation of a limited number of these novel conjugates failed to demonstrate any enhanced growth-inhibitory activity compared to the unconjugated drugs; sites of alkylation at tracts of multiple guanines were also unaffected. Attachment of additional residues at C-8 of the imidazotetrazines did not perturb the chemistry of activation of the bicyclic nucleus, and biological sequelae can be rationalized by invoking the liberation of a common, diffusible, reactive chemical intermediate, the methanediazonium ion.