(S)-methyl 2-amino-3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)propanoate | 1213330-83-6

• 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: (S)-methyl 2-amino-3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)propanoate
• 英文别名: methyl (S)-2-amino-3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)propanoate；methyl (2S)-2-amino-3-(2,3-dihydro-1,4-benzodioxin-6-yl)propanoate
• CAS: 1213330-83-6
• 化学式: C₁₂H₁₅NO₄
• 分子量: 237.255
• InChiKey: CJPILXKBUORNIC-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  70.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-methyl 2-amino-3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)propanoate 在 lithium hydroxide monohydrate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 19.0h， 生成 (S)-2-(2,5-dichlorobenzamido)-3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)propanoic acid
  参考文献：
  名称：

  发现一种用于治疗多发性骨髓瘤和三阴性乳腺癌的新型二肽基硼酸蛋白酶体抑制剂

  摘要：

  设计，合成和生物学研究了一系列新颖的二肽基硼酸化合物，以抑制20S蛋白酶体的β5亚基，几种化合物显示出高活性，IC 50值小于10 nM。这些化合物中的一些可有效抑制IC 50抑制多发性骨髓瘤（MM）癌细胞系值小于10 nM。据报道，对β2和β5亚基的抑制都大大增加了蛋白酶体抑制剂在实体瘤细胞中的细胞毒性，因此评估了其中一些化合物对β2亚基和实体瘤三阴性乳腺癌细胞MDA的抑制作用。 -MB-231。结果表明，三种化合物对β2亚基和三阴性乳腺癌细胞系MDA-MB-231均具有活性。的体内药物代谢动力学结果显示，化合物8吨有两个IG和iv给药良好的生物参数。的体内药效学试验表明，化合物8吨抑制了全血中的β5亚基更大地大于市售的MLN9708在不同的时间段使用相同的剂量。病理分析表明，与对照组相比，在三阴性乳腺癌异种移植小鼠模型的肿瘤中注射化合物8t导致肿瘤细胞坏死，细胞核浓缩，深层染色，细胞破

  DOI：

  10.1039/c8ob02668h
• 作为产物：
  描述：

  N-BOC-3-羟基-L-酪氨酸甲酯 在 potassium carbonate 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 (S)-methyl 2-amino-3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)propanoate
  参考文献：
  名称：

  A self-assembled tetrapeptide that acts as a “turn-on” fluorescent sensor for Hg2+ ion

  摘要：

  The tetrapeptide (Bz-Delta Phe(p-NPh2)-L-DOPA(protected)-L-Phe-L-Phe-OMe was designed to incorporate seven phenyl rings so that it's conformation, self-assembly and application in Hg2+ ions sensing could be studied. Peptide molecules adopted an overlapping beta-turn of type III/III conformation in crystals. The peptide showed a highly selective turn-on response towards mercuric ion over other metal ions with a 10-fold enhancement in fluorescence intensity. This intensity change coupled with the selectivity of the peptide towards mercury allowed us to demonstrate simple colorimetric dip sensing of Hg2+ ions. The technique provides a highly selective and effective way to detect He ions. The peptide also self-assembled into nanospheres with diameter ranges from 100 to 500 nm. Mercuric ion coordination enabled these peptide nanospheres to aggregate into well-defined nanoparticles. The enhanced fluorescence upon Hg2+ addition demonstrates that peptide scaffolds can be exploited in the development of different selective sensors. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2018.08.043

文献信息

• [EN] FLUOROISOQUINOLINE SUBSTITUTED THIAZOLE COMPOUNDS AND METHODS OF USE<br/>[FR] THIAZOLES SUBSTITUÉS PAR FLUOROISOQUINOLÉINE ET LEURS MÉTHODES D'APPLICATION
  申请人：AMGEN INC

  公开号：WO2010083246A1

  公开（公告）日：2010-07-22

  The invention relates to thiazole compounds of Formula (I) and compositions thereof useful for treating diseases mediated by protein kinase B (PKB) where the variables have the definitions provided herein. The invention also relates to the therapeutic use of such thiazole compounds and compositions thereof in treating disease states associated with abnormal cell growth, cancer, inflammation, and metabolic disorders.

  该发明涉及式(I)的噻唑化合物及其组合物，用于治疗由蛋白激酶B（PKB）介导的疾病，其中变量具有此处提供的定义。该发明还涉及在治疗与异常细胞生长、癌症、炎症和代谢紊乱相关的疾病状态中使用这种噻唑化合物和其组合物的治疗用途。
• Enantioselective Synthesis of Hydantoin and Diketopiperazine-Fused Tetrahydroisoquinolines via Pictet–Spengler Reaction
  作者：Shih-I Liu、Jia-Yun Haung、Indrajeet J. Barve、Sheng-Cih Huang、Chung-Ming Sun

  DOI：10.1021/acscombsci.9b00005

  日期：2019.4.8

  Pictet–Spengler reaction of (S)-2-amino-3-(3,4-dimethoxyphenyl)propanoates with various aldehydes to afford diastereomeric tetrahydroisoquinolines. Next step, the tetrahydroisoquinolines were further reacted with iso-, isothio-, or isoselenocyanates to construct hydantoin. Similarly, the diketopiperazine moiety was constructed by subjecting tetrahydroisoquinolines to a condensation reaction with chloroacetyl

  据报道从1 -Dopa对映异构地合成异-，异硫-和异亚硒基乙内酰脲和二酮哌嗪融合的四氢异喹啉。该路线由（S）-2-氨基-3-（3,4-二甲氧基苯基）丙酸酯与各种醛的Pictet-Spengler反应组成，以提供非对映体四氢异喹啉。下一步，使四氢异喹啉与异氰酸酯，异硫氰酸酯或异鲸蜡氰酸酯进一步反应以构建乙内酰脲。类似地，通过使四氢异喹啉与氯乙酰氯进行缩合反应，然后与各种伯胺进行亲核加成来构建二酮哌嗪部分。
• Pyroglutamic acid derivatives and related compounds which inhibit leukocyte adhesion mediated by VLA-4
  申请人：ELAN PHARMACEUTICALS, INC.

  公开号：EP1612215A1

  公开（公告）日：2006-01-04

  Disclosed are pyroglutamic acid derivatives and related compounds which bind VLA-4. Certain of these compounds also inhibit leukocyte adhesion and, in particular, leukocyte adhesion mediated by VLA-4. Such compounds are useful in the treatment of inflammatory diseases in a mammalian patient, e.g. human, such as asthma, Alzheimer's disease, atherosclerosis, AIDS dementia, diabetes, inflammatory bowel disease, rheumatoid arthritis, tissue transplantation, tumor metastasis and myocardial ischemia. The compounds can also be administered for the treatment of inflammatory brain diseases such as multiple sclerosis.

  本文披露了与VLA-4结合的吡咯烷酸衍生物和相关化合物。其中某些化合物还抑制白细胞粘附，特别是通过VLA-4介导的白细胞粘附。这些化合物在治疗哺乳动物患者（例如人类）的炎症性疾病中非常有用，如哮喘、阿尔茨海默病、动脉粥样硬化、艾滋病痴呆、糖尿病、炎症性肠病、类风湿性关节炎、组织移植、肿瘤转移和心肌缺血。这些化合物还可用于治疗多发性硬化等炎症性脑部疾病。
• One‐pot Synthesis of Isoquinoline‐Fused Isoquinolines via Intramolecular Hydroamination/Aza‐Claisen Type Rearrangement Cascade
  作者：Wei‐Jung Chiu、Jin‐Yu Chen、Shih‐I Liu、Indrajeet J. Barve、Wan‐Wen Huang、Chung‐Ming Sun

  DOI：10.1002/adsc.202001576

  日期：2021.6.8

  Pictet-Spengler reaction between α-amino acid esters and 2-alkynyl benzaldehydes to give isoquinoline intermediates. Subsequent gold-catalyzed intramolecular hydroamination furnishes isoquinoline-fused isoquinolines. The scope of this strategy is further extended to prepare multisubstituted isoquinoline-fused isoquinolines via subjecting the N-allylated isoquinoline intermediates to gold-catalyzed intramolecular

  报道了从 α-氨基酸酯和 2-炔基苯甲醛的异喹啉稠合异喹啉的一锅两步合成。该策略包括在 α-氨基酸酯和 2-炔基苯甲醛之间进行非常规的 Pictet-Spengler 反应，以得到异喹啉中间体。随后的金催化的分子内加氢胺化提供了异喹啉稠合的异喹啉。该策略的范围进一步扩展到通过对 N-烯丙基化异喹啉中间体进行金催化的分子内加氢胺化，然后进行 aza-Claisen 型重排来制备多取代的异喹啉稠合异喹啉。
• Compounds which inhibit leukocyte adhesion mediated by VLA-4
  申请人：Konradi W. Andrei

  公开号：US20050261293A1

  公开（公告）日：2005-11-24

  Disclosed are compounds which bind VLA-4. Certain of these compounds also inhibit leukocyte adhesion and, in particular, leukocyte adhesion mediated by VLA-4. Such compounds are useful in the treatment of inflammatory diseases in a mammalian patient, e.g., human, such as asthma, Alzheimer's disease, atherosclerosis, AIDS dementia, diabetes, inflammatory bowel disease, rheumatoid arthritis, tissue transplantation, tumor metastasis and myocardial ischemia. The compounds can also be administered for the treatment of inflammatory brain diseases such as multiple sclerosis.

  本发明涉及一种能够结合VLA-4的化合物。其中某些化合物还能够抑制白细胞黏附，特别是通过VLA-4介导的白细胞黏附。这样的化合物可用于治疗哺乳动物患者（例如人类）的炎症性疾病，例如哮喘、阿尔茨海默病、动脉硬化、艾滋病痴呆、糖尿病、炎性肠病、类风湿性关节炎、组织移植、肿瘤转移和心肌缺血。这些化合物还可用于治疗多发性硬化等炎症性脑部疾病。