3-(3,4,5-trimethoxyphenyl)propan-1-amine | 100252-79-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(3,4,5-trimethoxyphenyl)propan-1-amine
• 英文别名: 3-(3,4,5-trimethoxy-phenyl)-propylamine；3-(3,4,5-Trimethoxy-phenyl)-propylamin；Homomezcalin
• CAS: 100252-79-7
• 化学式: C₁₂H₁₉NO₃
• 分子量: 225.288
• InChiKey: LKINXVPAOSIISW-UHFFFAOYSA-N

物化性质

• 沸点：
  328.5±42.0 °C(Predicted)
• 密度：
  1.050±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  53.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(3,4,5-trimethoxyphenyl)propan-1-amine 、 6-氯嘌呤核苷 在 三乙胺 作用下， 以74%的产率得到(2R,3S,4R,5R)-2-Hydroxymethyl-5-{6-[3-(3,4,5-trimethoxy-phenyl)-propylamino]-purin-9-yl}-tetrahydro-furan-3,4-diol
  参考文献：
  名称：

  Dog coronary artery adenosine receptor. Structure of the N6-aryl subregion

  摘要：

  Previous structure-coronary vasoactivity correlations of the N6-alkyladenosine analogues of N6-[(R)-1-phenyl-2-propyl]adenosine, 1, support the hypothesis that the coronary artery A2 adenosine receptor contains an N6 region of specialized structure. The part of this receptor region that binds the 2-propyl moiety of 1 determines stereoselectivity and contributes to coronary vasoactivity. The present study uses 92 adenosine analogues containing an aryl group in the N6 substituent to test the hypothesis that the N6 receptor region contains an aryl subregion that binds the phenyl moiety of 1 and thereby contributes to its coronary vasoactivity. N6-Aralkyladenosines are often more potent than their alkyl congeners. Two methylene residues seem to provide optimum separation of the aryl group from N6. Among adenosines with semirigid N6 substituents, N6-[(1R,2S)-trans-2-phenylcyclohexyl]adenosine was uniquely active, evidence that when 1 occupies the receptor, the axis of the propyl C-1 to phenyl C-1 bond is nearly in the plane described by N6 and propyl C-1 and C-2. The torsion angle around this bond is unknown. Replacing the phenyl group of N6-2-phenethyladenosine with a thienyl or a 3-pyridyl group raises activity. The structure-activity relationships of the N6-(arylethyl)-, the N6-(arylmethyl)-, and the N6-phenyladenosines differ strinkingly from each other. Taken together, such results support the idea that the N6 region of the dog coronary artery A2 adenosine receptor includes an aryl subregion.

  DOI：

  10.1021/jm00156a016
• 作为产物：
  描述：

  3-(3,4,5-三甲氧基苯基)-1-丙醇 在 一水合肼 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 为溶剂， 反应 19.0h， 生成 3-(3,4,5-trimethoxyphenyl)propan-1-amine
  参考文献：
  名称：

  [EN] NOVEL ALLOSTERIC INHIBITORS OF PROTEASOME AND METHODS OF USE THEREOF
  [FR] NOUVEAUX INHIBITEURS ALLOSTÉRIQUES DU PROTÉASOME ET MÉTHODES D'UTILISATION ASSOCIÉES

  摘要：

  本发明涉及一般的新型蛋白酶体活性的变构调节剂，其制备和使用方法，以及其制药组合物。具体地，揭示了含有1-氧代芳酰基和疏水性酯侧链的哌啶-2-羧酸衍生物作为蛋白酶体2S活性的变构抑制剂，以及作为治疗蛋白酶体相关疾病的治疗剂在一个受体中的应用。

  公开号：

  WO2014201405A1

文献信息

• 8-Hydroxyquinolin-2(1H)-one analogues as potential β2-agonists: Design, synthesis and activity study
  作者：Gang Xing、Zhengxing Zhi、Ce Yi、Jitian Zou、Xuefeng Jing、Anthony Yiu-Ho Woo、Bin Lin、Li Pan、Yuyang Zhang、Maosheng Cheng

  DOI：10.1016/j.ejmech.2021.113697

  日期：2021.11

  to plasmalemmal β2-adrenoceptors causing cAMP accumulation are widely used as bronchodilators in chronic respiratory diseases. Here, we designed and synthesized a group of 8-hydroxyquinolin-2(1H)-one analogues and studied their β2-agonistic activities with a cellular cAMP assay. Compounds B05 and C08 were identified as potent (EC50 < 20 pM) and selective β2-agonists among the compounds tested. They

  与导致 cAMP 积累的质膜β 2 -肾上腺素受体结合的β 2 -激动剂被广泛用作慢性呼吸系统疾病中的支气管扩张剂。在这里，我们设计并合成了一组 8-hydroxyquinolin-2(1 H )-one 类似物，并通过细胞 cAMP 测定研究了它们的 β 2 -激动活性。在测试的化合物中，化合物B05和C08被确定为有效的 (EC 50  < 20 pM) 和选择性 β 2 -激动剂。它们表现为部分 β 2β-激动剂在非过表达的 HEK293 细胞中，并在离体豚鼠气管条制剂中具有快速平滑肌松弛作用和长作用持续时间。综上所述，B05和C08是具有潜在适用于慢性呼吸道疾病的 β 2 -激动剂。
• Discovery and Identification of Novel 5-Hydroxy-4<i>H</i>-benzo[1,4]oxazin-3-one Derivatives as Potent β₂-Adrenoceptor Agonists through Structure-Based Design, Synthesis, and Biological Evaluation
  作者：Gang Xing、Zhenli Li、Zhengxing Zhi、Ce Yi、Ruiwen Zhang、Huali Yang、Yuyang Zhang、Bin Lin、Yang Liu、Li Pan、Maosheng Cheng

  DOI：10.1021/acs.jmedchem.3c02074

  日期：2024.2.22

  optimizing β2-agonistic activity and selectivity remains essential for achieving favorable therapeutic outcomes. A structure-based molecular design workflow was employed to discover a novel class of β2 agonists featuring a 5-hydroxy-4H-benzo[1,4]oxazin-3-one scaffold, which potently stimulated β2 adrenoceptors (β2-ARs). Screening for the β2-agonistic activity and selectivity led to the identification of

  尽管β 2 受体激动剂对于治疗慢性呼吸系统疾病至关重要，但优化β 2 受体激动剂的活性和选择性对于获得良好的治疗结果仍然至关重要。采用基于结构的分子设计工作流程来发现一类新型的 β2 激动剂，其特点是 5-羟基-4H-苯并[1,4]恶氮嗪-3-酮支架，可有效刺激β 2 个肾上腺素能受体 （β2-ARs）。筛选 β2-激动活性和选择性导致鉴定出化合物 A19 （EC50 = 3.7 pM），该化合物在含有内源性 β2-AR 的 HEK-293 细胞中起部分 β2-激动剂的作用。化合物 A19 对离体豚鼠气管条表现出显着的松弛作用、快速起效时间 （Ot50 = 2.14 min） 和长作用持续时间 （>12 h），以及有利的体内药代动力学特性，使 A19 适合吸入给药。此外，A19 抑制了 COPD 大鼠模型中炎性细胞因子和白细胞的上调，并改善了肺功能，从而表明 A19 是进一步研究的潜在 β2
• Allosteric inhibitors of proteasome and methods of use thereof
  申请人：THE BOARD OF REGENTS OF THE UNIVERSITY OF TEXAS SYSTEM

  公开号：US10167259B2

  公开（公告）日：2019-01-01

  The present invention relates generally to novel allosteric regulators of proteasome activity, methods for preparation and use, and pharmaceutical compositions thereof. Specifically piperidine-2-carboxylic acid derivatives containing 1-oxo-aroyl group and a lipophilic ester side chain are disclosed as allosteric inhibitors of proteasome 2S activity, and as therapeutic agents for the treatment of proteasome-associated disorders in a subject.

  本发明一般涉及蛋白酶体活性的新型异位调节剂、制备和使用方法及其药物组合物。具体而言，本发明公开了含有 1-氧代-芳酰基和亲油酯侧链的哌啶-2-羧酸衍生物，作为蛋白酶体 2S 活性的异构抑制剂，以及用于治疗受试者蛋白酶体相关疾病的治疗剂。
• Notes - Mescaline Anaologs. VI. Mescaline Homologs
  作者：F. Benington、R. C. Morin、L. C. Clark, Jr.

  DOI：10.1021/jo01118a635

  日期：1956.12.1
• Belletire, J. L.; Fry, D. F., Synthetic Communications, 1988, vol. 18, # 1, p. 29 - 36
  作者：Belletire, J. L.、Fry, D. F.

  DOI：——

  日期：——