L-2',6'-dimethylphenylalanine | 103854-26-8

• 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: L-2',6'-dimethylphenylalanine
• 英文别名: α-(S)-2',6'-dimethylphenylalanine；2',6'-dimethyl-L-alanine；(2S)-2-azaniumyl-3-(2,6-dimethylphenyl)propanoate
• CAS: 103854-26-8
• 化学式: C₁₁H₁₅NO₂
• 分子量: 193.246
• InChiKey: VEQOZHOWFAVBOO-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2922499990

反应信息

• 作为反应物：
  描述：

  L-2',6'-dimethylphenylalanine 在 盐酸 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.5h， 生成 N^α-tert-butyloxycarbonyl-2',6'-dimethyl-L-tyrosyl-L-prolyl-2',6'-dimethyl-L-phenylalanyl-L-phenylalanylamide
  参考文献：
  名称：

  Bifunctional [2‘,6‘-Dimethyl-l-tyrosine]endomorphin-2 Analogues Substituted at Position 3 with Alkylated Phenylalanine Derivatives Yield Potent Mixed μ-Agonist/δ-Antagonist and Dual μ-Agonist/δ-Agonist Opioid Ligands

  摘要：

  Endomorphin-2 (H-Tyr-Pro-Phe-Phe-NH2) and [Dmt(1)]EM-2 (Dmt = 2',6'-dimethyl-L-tyrosine) analogues, containing alkylated Phe(3) derivatives, 2'-monomethyl (2, 2'), 3',5'- and 2',6'-dimethyl (3, 3', and 4', respectively), 2',4',6'-trimethyl (6, 6'), 2'-ethyl-6'-methyl (7, 7'), and 2'-isopropyl-6'-methyl (8, 8') groups or Dmt (5, 5'), had the following characteristics: (i) [Xaa(3)]EM-2 analogues exhibited improved mu- and delta-opioid receptor affinities. The latter, however, were inconsequential (K-i(delta) = 491-3451 nM). (ii) [Dmt(1),Xaa(3)]EM-2 analogues enhanced mu- and delta-opioid receptor affinities (K-i(mu) = 0.069-0.32 nM; K-i(delta) = 1.83-99.8 nM) without kappa-opioid receptor interaction. (iii) There were elevated mu-bioactivity (IC50 = 0.12-14.4 nM) and abolished delta-agonism (IC50 > 10 mu M in 2', 3', 4', 5', 6'), although 4' and 6' demonstrated a potent mixed mu-agonism/delta-antagonism (for 4', IC50 mu = 0.12 and pA(2) = 8.15; for 6', IC50 mu = 0.21 nM and pA(2) = 9.05) and 7' was a dual mu-agonist/delta-agonist (IC50 mu = 0.17 nM; IC50 delta = 0.51 nM).

  DOI：

  10.1021/jm061238m
• 作为产物：
  描述：

  1,3-二甲基-2-碘苯 在 palladium on activated charcoal 盐酸 、 palladium diacetate 、 sodium hydroxide 、 氢气 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 三(邻甲基苯基)磷 作用下， 以 1,4-二氧六环 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 70.0 ℃ 、405.3 kPa 条件下， 反应 45.0h， 生成 L-2',6'-dimethylphenylalanine
  参考文献：
  名称：

  Enkephalin analogues with 2′,6′-dimethylphenylalanine replacing phenylalanine in position 4

  摘要：

  Four Leu-enkephalin (Enk) analogues containing 2'.6'-dimethyphenylalanine (Dmp) in position 4 were prepared and tested for their receptor binding and biological activities. Among the analogues prepared, [2', 6'-dimethvltyrosine(1), D-Dmp(4)]Enk was found to be an antagonist toward mu and delta opioid receptors with pA(2) values of 6.90 and 5.57, respectively. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00665-x

文献信息

• Angiotensin-1-Receptor Antagonists
  申请人：Ferring B.V.

  公开号：US20170349629A1

  公开（公告）日：2017-12-07

  In one aspect, this disclosure features compounds of formula (I) or a pharmaceutically acceptable salt thereof: AA1-Arg-Val-AA4-AA5-His-Pro-AA8-OH   (I), in which AA1, AA4, AA5, and AA8 are defined in the specification. The compounds of formula (I) can be used to treat hypertension (e.g., hypertension induced by pregnancy), preeclampsia, or a renal disease induced by pregnancy.

  在一个方面，这个披露涉及到式(I)的化合物或其药用盐： AA1-Arg-Val-AA4-AA5-His-Pro-AA8-OH (I)， 其中AA1，AA4，AA5和AA8在规范中有定义。式(I)的化合物可用于治疗高血压（例如，妊娠引起的高血压），子痫前期，或妊娠引起的肾脏疾病。
• Peptide Derivative
  申请人：Sakurada Shinobu

  公开号：US20080009448A1

  公开（公告）日：2008-01-10

  A pharmaceutical composition comprising a peptide derivative or its pharmaceutical equivalent salt having a general formula, R 1 N═C(R 2 )-AA 1 -AA 2 -AA 3 -AA 4 -Y, in which R 1 is such as a hydrogen, R 2 is such as a methyl group, Y is such as a methylamino group, AA 1 is such as a tyrosine group, AA 2 is such as a D-arginine group, AA 3 is such as a phenylalanine group, and AA 4 is such as a N-methyllysine group has analgesic activity against a variety of pains on both subcutaneous and oral administration.

  一种包括肽衍生物或其药用等效盐的药物组合物，其具有一般式R1N═C(R2)-AA1-AA2-AA3-AA4-Y，其中R1为氢，R2为甲基基团，Y为甲基氨基基团，AA1为酪氨酸基团，AA2为D-精氨酸基团，AA3为苯丙氨酸基团，AA4为N-甲基赖氨酸基团，在皮下和口服给药时对各种疼痛具有镇痛活性。
• AROMATIC-CATIONIC PEPTIDES AND USES OF SAME
  申请人：Szeto Hazel H.

  公开号：US20120329730A1

  公开（公告）日：2012-12-27

  The disclosure provides aromatic-cationic peptide compositions and methods of preventing or treating disease using the same. The methods comprise administering to the subject an effective amount of an aromatic-cationic peptide to subjects in need thereof.

  该披露提供了芳香性阳离子肽组合物以及使用这些组合物预防或治疗疾病的方法。该方法包括向需要的对象施用有效量的芳香性阳离子肽。
• RAPAFUCIN DERIVATIVE COMPOUNDS AND METHODS OF USE THEREOF
  申请人：The Johns Hopkins University

  公开号：US20210094933A1

  公开（公告）日：2021-04-01

  The present disclosure provides macrocyclic compounds inspired by the immunophilin ligand family of natural products FK506 and rapamycin. The generation of a Rapafucin library of macrocyles that contain FK506 and rapamycin binding domains should have great potential as new leads for developing drugs to be used for treating diseases.

  本公开提供了受免疫蛋白配体家族FK506和雷帕霉素天然产物启发的大环化合物。生成包含FK506和雷帕霉素结合结构域的Rapafucin大环化合物库，应具有作为治疗疾病新药的潜力。
• Synthesis of 2,6-Dimethyltyrosine-Like Amino Acids through Pinacolinamide-Enabled C–H Dimethylation of 4-Dibenzylamino Phenylalanine
  作者：Davide Illuminati、Anna Fantinati、Tiziano De Ventura、Daniela Perrone、Chiara Sturaro、Valentina Albanese、Erika Marzola、Virginia Cristofori、Julie Oble、Giovanni Poli、Claudio Trapella

  DOI：10.1021/acs.joc.1c02527

  日期：2022.3.4

  carrying methyl groups at positions 2 and 6 and diverse functionalities at position 4 has been achieved. The approach, which took advantage of a Pd-catalyzed directed C–H dimethylation of picolinamide derivatives, allowed the electronic and steric properties of the resulting amino acid derivatives to be altered by appending a variety of electron-withdrawing, electron-donating, or bulky groups.

  已经实现了在 2 位和 6 位带有甲基基团和在 4 位具有多种官能团的NH -Boc-或NH -Fmoc-保护的 L-苯丙氨酸的小型文库的合成。该方法利用 Pd 催化的甲基吡啶酰胺衍生物的定向 C-H 二甲基化，通过添加各种吸电子、给电子或庞大的物质，可以改变所得氨基酸衍生物的电子和空间特性。团体。