H-Leu-NH2 * trifluoroacetic acid | 77313-69-0

• 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: H-Leu-NH2 * trifluoroacetic acid
• 英文别名: (2S)-2-amino-4-methylpentanamide;2,2,2-trifluoroacetic acid
• CAS: 77313-69-0
• 化学式: C₂HF₃O₂*C₆H₁₄N₂O
• 分子量: 244.214
• InChiKey: CTNQBXARBXTCHX-JEDNCBNOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.48
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  106
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-(3-苯基-1,2,4-噁二唑)丙酸盐 、 H-Leu-NH2 * trifluoroacetic acid 在 TEA 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 (S)-4-Methyl-2-[3-(3-phenyl-[1,2,4]oxadiazol-5-yl)-propionylamino]-pentanoic acid amide
  参考文献：
  名称：

  Synthesis, anti-inflammatory and antimicrobial activities of new 1,2,4-oxadiazoles peptidomimetics

  摘要：

  A new series of 1,2,4-oxadizoles 6a-g have been synthesised in good yields using the peptide synthesis strategy. The prepared compounds were tested for anti-inflammatory and antimicrobial activities. The anti-inflammatory activities were determined in the rat paw oedema induced by carrageenin. Compounds 6a, c, f and g (i.v.) significantly inhibited the rat paw oedema induced by carrageenin depending upon the dose employed. The compounds were also evaluated for their in vitro antimicrobial activity. Some compounds were found to have significant activity against Gram positive and Gram negative microorganisms. (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(00)00099-9
• 作为产物：
  描述：

  BOC-L-亮氨酸 在 N-甲基吗啉 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 H-Leu-NH2 * trifluoroacetic acid
  参考文献：
  名称：

  新型Fubinaca / Rimonabant杂种作为内源性大麻素系统调节剂。

  摘要：

  大麻素系统新型调节剂的发现是药物化学中的当前主题。在本文中，我们报告了9种新颖的羧酰胺，它们被设计为Fubinaca家族化合物和Rimonabant的杂化物。通过将1-苄基-2，5-二氯吲唑-3-羧酸与带有疏水侧链和三个不同C-末端的不同氨基酸连接而获得这些杂化物。新的化学实体在体外进行了测试，以通过受体结合测定和[ 35S]GTPγS刺激试验以揭示其亲和力和效力。我们发现，所有化合物均能够在低纳摩尔范围内结合大麻素受体，并对CB1大麻素受体具有明显的选择性。其中一些是完全激动剂，而另一些则是部分激动剂。这些分子有可能被用作减肥药，止吐药和止痛药。

  DOI：

  10.1007/s00726-018-2636-1

文献信息

• Studies on peptides. CXVI. Synthesis of the protected docosapeptide corresponding to the C-terminal portion of human growth hormone releasing factor (GRF, somatocrinin).
  作者：NOBUTAKA FUJII、MASANORI SHIMOKURA、KENICHI AKAJI、SHINYA KIYAMA、HARUAKI YAJIMA

  DOI：10.1248/cpb.32.510

  日期：——

  As a starting material for the solution synthesis of a tetratetracontapeptide amide corresponding to the entire sequence of growth hormone releasing factor derived from human pancreatic tumor, a C-terminal-protected docosapeptide amide (positions 23-44) was synthesized by successive azide condensation of three peptide fragments (positions 33-44, 28-32, and 23-27). Amino acid derivatives bearing protecting groups removable by trifluoromethanesulfonic acid were employed; i.e., benzyloxycarbonyl (Z), benzyl (Bzl), and mesitylene-2-sulfonyl (Mts).

  作为溶液合成对应于从人类胰腺肿瘤中提取的生长激素释放因子整个序列的四重四肽酰胺的起始原料，通过连续缩合三个肽片段（位置 33-44、28-32 和 23-27）的叠氮化物，合成了一个 C 端受保护的二十二肽酰胺（位置 23-44）。采用的氨基酸衍生物含有可被三氟甲磺酸去除的保护基团，即苄氧羰基（Z）、苄基（Bzl）和介苯-2-磺酰基（Mts）。
• Synthesis of gem-diamino derivatives on solid support
  作者：Sonia Cantel、Damien Boeglin、Marc Rolland、Jean Martinez、Jean-Alain Fehrentz

  DOI：10.1016/s0040-4039(03)00925-0

  日期：2003.6

  Anchoring of an α-amino-acid amide residue by its amine function to a carbamate resin followed by primary amide Hofmann rearrangement led to a gem-diamino residue linked to the resin. The generated primary amine could be acylated with various carboxylic compounds offering a large variety of molecules. Furthermore, this new solid-phase strategy allowed a reliable synthesis of a gem-diamino monomeric

  α-氨基酸酰胺残基的胺官能团将其锚定到氨基甲酸酯树脂上，然后伯酰胺霍夫曼重排导致与树脂相连的gem -diamino残基。产生的伯胺可以被提供多种分子的各种羧酸化合物酰化。此外，由于单氨基甲酸酯保护的宝石-二氨基烷基衍生物的有限的稳定性，这种新的固相策略允许可靠地合成宝石-二氨基单体残基，该残基在溶液中不易获得。
• Synthesis and antitumour evaluation of peptidyl-like derivatives containing the 1,3-benzodioxole system
  作者：Diogo Rodrigo de Magalhães Moreira、Ana Cristina Lima Leite、Paulo Michel Pinheiro Ferreira、Patrícia Marçal da Costa、Letícia Veras Costa Lotufo、Manoel Odorico de Moraes、Dalci José Brondani、Claudia do Ó Pessoa

  DOI：10.1016/j.ejmech.2006.10.007

  日期：2007.3

  In the scope of a research program aiming at the synthesis and pharmacological evaluation of novel possible antitumour prototype compounds, we described in this paper the synthesis of peptidyl-like derivatives containing the 1,3-benzodioxole system. The proliferation inhibitors tested against tumour cell lines identified the derivatives tyrosine (4f) and lysine (4g) as the most active among them, presenting IC50 values in micromolar range and are more active than Safrole. For the study on the embryonic development, Safrole did not show any selectivity in this latter assay, which indicates that Safrole acts as a 'cell cycle-nonspecific' inhibitory agent. However, compound M presented a fair antimitotic effect, mainly on third cleavage and blastulae stages (38% and 1.7% of normal development, at 10 mu g/mL), suggesting a time-dependent activity and a 'cell cycle-specific' agent action. Neither derivatives revealed hemolytic action in assay with mouse erythrocytes. (c) 2006 Elsevier Masson SAS. All rights reserved.
• [EN] DIPEPTIDE LIGANDS OF TSPO THAT POSSESS NEUROPSYCHOTROPIC ACTIVITY<br/>[FR] LIGANDS DIPEPTIDIQUES TSPO AYANT UNE ACTION NEUROPSYCHOTROPE<br/>[RU] ДИПЕПТИДНЫЕ ЛИГАНДЫ TSPO, ОБЛАДАЮЩИЕ НЕЙРОПСИХОТРОПНОЙ АКТИВНОСТЬЮ
  申请人：FEDERAL STATE BUDGETARY INSTITUTION RES ZAKUSOV INSTITUTE OF PHARMACOLOGY FSBI ZAKUSOV INSTITUTE OF

  公开号：WO2020117099A1

  公开（公告）日：2020-06-11

  Изобретение относится к области биологически активных соединений и касается новых дипептидов формулы, R1-C(O)-X-AK1-Y-АК2-R2, где X=L или D конфигурация, Y=L или D конфигурация; АК1 Trp или Gly; АК2 Leu или Gly; R1=C6H5-CH2- или С6Н5-(СН2)2- или СН3-(СН2)4-; R2=OH или ОСН3 или NH2 или NHCH3 обладающие спектром нейропсихотропной активности, в частности, анксиолитической и антидепрессивной. Анксиолитическая активность заявляемых соединений была выявлена в дозах 0,1-1,0 мг/кг, а для соединения C6H5-(CH2)2C(O)-L-Trp-L-Leu-NH2 в дозах 0,01-5,00 мг/кг, при внутрибрюшинном введении у мышей BALB/c в тесте открытого поля со световой вспышкой в условиях эмоционально-стрессового воздействия. Дополнительно анксиолитическая активность для соединения C6H5-(CH2)2C(O)-L-Trp-L-Leu-NH2 в дозах 0,1-1,0 мг/кг была выявлена в тесте приподнятого крестообразного лабиринта на мышах ICR. С использованием селективного антагониста PK11195 доказано, что анксиолитический эффект соединения C6H5-(CH2)2C(O)-L-Trp-L-Leu-NH2 зависит от связывания с 18 kDa белком TSPO. Антидепрессивная активность для соединения С6Н5-(СН2)2С(O)-L-Trp-L-Leu-NH2 была выявлена в дозах 0,01-0,05 мг/кг при внутрибрюшинном введении у мышей BALB/c в тесте вынужденного плавания по Порсолту.