tert-butyl (S)-(1-(methoxy(methyl)amino)-3-(4-methoxyphenyl)-1-oxopropan-2-yl)carbamate | 139183-59-8

• 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: tert-butyl (S)-(1-(methoxy(methyl)amino)-3-(4-methoxyphenyl)-1-oxopropan-2-yl)carbamate
• 英文别名: N-(t-butoxycarbonyl)-O-methyl-L-tyrosine N-methoxy-N-methylamide；tert-butyl N-[(2S)-1-[methoxy(methyl)amino]-3-(4-methoxyphenyl)-1-oxopropan-2-yl]carbamate
• CAS: 139183-59-8
• 化学式: C₁₇H₂₆N₂O₅
• 分子量: 338.404
• InChiKey: AAHUYCZMASAMHX-AWEZNQCLSA-N

物化性质

• 密度：
  1.121±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  77.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl (S)-(1-(methoxy(methyl)amino)-3-(4-methoxyphenyl)-1-oxopropan-2-yl)carbamate 在 lithium aluminium tetrahydride 、 三乙胺 、 三氟乙酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 (S)-2-Amino-N-[(S)-2-ethylcarbamoyl-2-hydroxy-1-(4-methoxy-benzyl)-ethyl]-3-methyl-butyramide
  参考文献：
  名称：

  Novel cell-penetrating α-keto-amide calpain inhibitors as potential treatment for muscular dystrophy

  摘要：

  Dipeptide-derived alpha-keto-amide compounds with potent calpain inhibitory activity have been identified. These reversible covalent inhibitors have IC50 values down to 25 nM and exhibit greatly improved activity in muscle cells compared to the reference compound MDL28170. Several novel calpain inhibitors have shown positive effects on histological parameters in an animal model of Duchenne muscular dystrophy demonstrating their potential as a treatment option for this fatal disease. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.08.064
• 作为产物：
  描述：

  Boc-O-甲基-L-酪氨酸 、 N-甲基-N-甲氧基胺盐酸盐 在 N-甲基吗啉 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到tert-butyl (S)-(1-(methoxy(methyl)amino)-3-(4-methoxyphenyl)-1-oxopropan-2-yl)carbamate
  参考文献：
  名称：

  Novel cell-penetrating α-keto-amide calpain inhibitors as potential treatment for muscular dystrophy

  摘要：

  Dipeptide-derived alpha-keto-amide compounds with potent calpain inhibitory activity have been identified. These reversible covalent inhibitors have IC50 values down to 25 nM and exhibit greatly improved activity in muscle cells compared to the reference compound MDL28170. Several novel calpain inhibitors have shown positive effects on histological parameters in an animal model of Duchenne muscular dystrophy demonstrating their potential as a treatment option for this fatal disease. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.08.064

文献信息

• Probing α‐Amino Aldehydes as Weakly Acidic Pronucleophiles: Direct Access to Quaternary α‐Amino Aldehydes by an Enantioselective Michael Addition Catalyzed by Brønsted Bases
  作者：Ane García‐Urricelqui、Abel Cózar、Antonia Mielgo、Claudio Palomo

  DOI：10.1002/chem.202004468

  日期：2021.2

  The high tendency of α‐amino aldehydes to undergo 1,2‐additions and their relatively low stability under basic conditions have largely prevented their use as pronucleophiles in the realm of asymmetric catalysis, particularly for the production of quaternary α‐amino aldehydes. Herein, it is demonstrated that the chemistry of α‐amino aldehydes may be expanded beyond these limits by documenting the first

  α-氨基醛很容易发生1,2-加成反应，并且在碱性条件下具有相对较低的稳定性，这在很大程度上阻止了它们在不对称催化领域用作亲核试剂，特别是在生产季α-氨基醛方面。本文证明了α-氨基醛的化学性质可能超出了这些限制，方法是记录α-支链α-氨基醛与硝基烯烃的首次直接α-烷基化反应。该反应产生具有多达非对映和对映选择性的稠密的官能化产物，该产物带有多达两个的四级和三级邻位立体中心。DFT建模提出了这样的建议，即在NH基团与起始α-氨基醛中的羰基氧原子之间的分子内氢键是反应立体控制的关键。
• [EN] UREA DERIVATIVE OR PHARMACOLOGICALLY ACCEPTABLE SALT THEREOF<br/>[FR] DÉRIVÉ D'URÉE OU SEL PHARMACOLOGIQUEMENT ACCEPTABLE DE CE DERNIER
  申请人：KYORIN SEIYAKU KK

  公开号：WO2016189877A1

  公开（公告）日：2016-12-01

  The present invention provides a urea compound or a pharmacologically acceptable salt thereof that has a formyl peptide receptor like 1 (hereinafter may be abbreviated as FPRL1) agonist effect, a pharmaceutical composition containing the urea compound or the pharmacologically acceptable salt thereof, and a pharmaceutical use thereof. It has been found that a urea derivative represented by the general formula (I) below or a pharmacologically acceptable salt thereof has a superior FPRL1 agonist effect. Compound (I) or a pharmacologically acceptable salt thereof is highly useful for treatment, prevention, or suppression of inflammatory diseases, chronic airway diseases, cancers, septicemia, allergic symptoms, HIV retrovirus infection, circulatory disorders, neuroinflammation, nervous disorders, pains, prion diseases, amyloidosis, immune disorders and the like.

  本发明提供了一种尿素化合物或其药理学上可接受的盐，具有类似甲酰肽受体1（以下简称为FPRL1）的激动剂作用，含有该尿素化合物或其药理学上可接受的盐的药物组合物，以及其药用。已发现下述一般式（I）所代表的尿素衍生物或其药理学上可接受的盐具有优越的FPRL1激动剂作用。化合物（I）或其药理学上可接受的盐对于治疗、预防或抑制炎症性疾病、慢性气道疾病、癌症、败血症、过敏症状、HIV逆转录病毒感染、循环障碍、神经炎症、神经障碍、疼痛、朊病、淀粉样变性、免疫障碍等方面非常有用。
• Compounds, compositions and methods for treatment of parasitic infections
  申请人：——

  公开号：US20020107266A1

  公开（公告）日：2002-08-08

  Compounds and pharmaceutical compositions useful as anti-parasitic agents agents, particularly in the treatment, prevention or amelioration of one or more symptoms of malaria or Chagas' disease, are provided. In particular, methods of modulating the activity of falcipain or cruzain, preferably inhibiting falcipain or cruzain, with the compounds and compositions are provided.

  提供了作为抗寄生虫药剂的化合物和药物组合物，特别是用于治疗、预防或缓解疟疾或充满病症状之一的药剂。具体而言，提供了利用这些化合物和组合物调节falcipain或cruzain活性的方法，优选抑制falcipain或cruzain的方法。
• Acetic acid derivatives
  申请人：Hoffmann-La Roche Inc.

  公开号：US05726185A1

  公开（公告）日：1998-03-10

  Acetic acid derivatives of the formula ##STR1## wherein L, M, T and Q have the significance given in the description, can be used for the treatment or prophylaxis of illnesses which are caused by the binding of adhesive proteins to blood platelets and by blood platelet aggregation and cell-cell adhesion, and are manufactured by cleaving protecting groups in the corresponding protected compounds or by converting the cyano group into the amidino group in corresponding nitriles.

  公式为##STR1##的乙酸衍生物，其中L、M、T和Q的含义如描述中所示，可用于治疗或预防由粘附蛋白结合到血小板以及血小板聚集和细胞间黏附引起的疾病，并且可以通过裂解相应保护化合物中的保护基或将相应腈化合物中的氰基转化为氨基亚甲基基团来制造。
• [EN] INCREASING BLOOD-BRAIN BARRIER PERMEABILITY WITH PERMEABILIZER PEPTIDES
  申请人：ALKERMES, INC.

  公开号：WO1992018529A1

  公开（公告）日：1992-10-29

  (EN) Peptides called receptor mediated permeabilizers (RMP) increase the permeability of the blood/brain barrier to molecules such as therapeutic agents or diagnostic agents. The permeabilizer A-7 or conformational analogues can be intravenously coadministered to a host together with molecules whose desired destination is the interstitial fluid compartment of the brain. Alternatively, the permeabilizer A-7 or conformational analogues can be administered sequentially with the molecule(s) of interest and these molecules can also be administered by routes other than intravascular. The permeabilizer A-7 or conformational analogues allow these molecules to penetrate the blood-brain barrier and arrive in the interstitial fluid.(FR) On a découvert que des peptides appelés perméabiliseurs propagés par récepteur (PPR) augmentent la perméabilité de la barrière hémato-encéphalique à des molécules telles que des agents thérapeutiques ou de diagnostic. On peut administrer par voie intraveineuse chez un hôte, le perméabiliseur A-7 ou des analogues de ce dernier ayant la même conformation en même temps que des molécules dont la destination voulue est le compartiment du liquide interstitiel du cerveau. Dans un autre mode d'exécution on peut administrer de manière séquentielle le perméabiliseur A-7 ou ses analogues de même conjointement avec la ou les molécules en question, lesdites molécules pouvant également être administrées par d'autres voies d'administration que la voie intraveineuse. Le perméabiliseur A-7 ou ses analogues de même conformation permettent à ces molécules de traverser la barrière hémato-encéphalique et d'arriver dans le liquide interstitiel.

  肽类受体介导的渗透剂（RMP）可增加血脑屏障对治疗剂或诊断剂等分子的渗透性。渗透剂A-7或构象类似物可以与需要到达脑间质液区域的分子一起静脉共同给予宿主。或者，渗透剂A-7或构象类似物可以与感兴趣的分子顺序给予，这些分子也可以通过除静脉途径以外的途径给予。渗透剂A-7或构象类似物使这些分子能够穿过血脑屏障并到达脑间质液。