N-(2-phenylethyl)-3-aminopropionic acid | 173406-18-3

• 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: N-(2-phenylethyl)-3-aminopropionic acid
• 英文别名: β-Phenethyl-β-alanine；3-(2-Phenylethylazaniumyl)propanoate
• CAS: 173406-18-3
• 化学式: C₁₁H₁₅NO₂
• mdl: MFCD08443533
• 分子量: 193.246
• InChiKey: DYJFVIXCJFSAFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-phenylethyl)-3-aminopropionic acid 在 磷酸 、 三氯化磷 作用下， 以 氯苯 为溶剂， 反应 3.0h， 以50%的产率得到(1-Hydroxy-3-phenethylamino-1-phosphono-propyl)-phosphonic acid
  参考文献：
  名称：

  Highly Potent Geminal Bisphosphonates. From Pamidronate Disodium (Aredia) to Zoledronic Acid (Zometa)

  摘要：

  Bisphosphonates (BP) are pyrophosphate analogues in which the oxygen in P-O-P has been replaced by a carbon, resulting in a metabolically stable P-C-P structure. Pamidronate (1b, Novartis), a second-generation BP, was the starting point for extensive SAR studies. Small changes of the structure of pamidronate lead to marked improvements of the inhibition of osteoclastic resorption potency. Alendronate (1c, MSD), with an extra methylene group in the N-alkyl chain, and olpadronate (1h, Gador), the N,N-dimethyl analogue, are about 10 times more potent than pamidronate. Extending one of the N-methyl groups of olpadronate to a pentyl substituent leads to ibandronate (1k, Roche, Boehringer-Mannheim), which is the most potent close analogue of pamidronate. Even slightly better antiresorptive potency is achieved with derivatives having a phenyl group linked via a short aliphatic tether of three to four atoms to nitrogen, the second substituent being preferentially a methyl group (e.g., 4g, 4j, 5d, or 5r). The most potent BPs are found in the series containing a heteroaromatic moiety (with at least one nitrogen atom), which is linked via a single methylene group to the geminal bisphosphonate unit. Zoledronic acid (6i), the most potent derivative, has an ED50 of 0.07 mg/kg in the TPTX in vivo assay after sc administration. It not only shows by far the highest therapeutic ratio when comparing resorption inhibition with undesired inhibition of bone mineralization but also exhibits superior renal tolerability. Zoledronic acid (6i) has thus been selected for clinical development under the registered trade name Zometa. The results of the clinical trials indicate that low doses are both efficacious and safe for the treatment of tumor-induced hypercalcemia, Paget's disease of bone, osteolytic metastases, and postmenopausal osteoporosis.

  DOI：

  10.1021/jm020819i
• 作为产物：
  描述：

  methyl 3-propionate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 N-(2-phenylethyl)-3-aminopropionic acid
  参考文献：
  名称：

  N-, α-, and β-Substituted 3-Aminopropionic acids: design, syntheses and antiseizure activities

  摘要：

  A treatment for epilepsy is proposed based on analogues of 3-aminopropionic acid (beta-alanine), a putative neurotransmitter in the central nervous system (CNS). A model three point pharmacophore was proposed based on modelling data obtained from the study of antagonists for both the glial gamma-aminobutyric acid (GABA)-uptake site and the glycine co-agonist site of N-methyl-D-aspartate (NMDA) receptor. Three series of 3-aminopropionic acids containing, N-, alpha-, and beta-substituents, were designed and synthesized to probe the position and the size of a lipophilic binding pocket within the proposed pharmacophore. These analogues were tested in vivo for both their antiseizure activities and their neurologic toxicities. Among the fourteen novel 3-aminopropionic acids synthesized, eight were found to have promising antiseizure activity. This study shows that substitution on the N-terminus confers the greatest antiseizure activity, particularly against pilocarpine-induced seizures. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00330-9

文献信息

• [EN] AZABICYCLIC(THIO)AMIDES AS FUNGICIDAL COMPOUNDS<br/>[FR] (THIO)AMIDES AZABICYCLIQUES EN TANT QUE COMPOSÉS FONGICIDES
  申请人：BAYER AG

  公开号：WO2021233861A1

  公开（公告）日：2021-11-25

  The present invention relates to azabicyclic (thio)amide compounds and the uses thereof for controlling phytopathogenic microorganisms such as phytopathogenic fungi. It also relates to processes and intermediates for preparing these compounds

  本发明涉及吡啶环(硫)酰胺化合物及其用途，用于控制植物病原微生物，如植物病原真菌。它还涉及制备这些化合物的过程和中间体。
• [EN] TRISUBSTITUTEDSILYLMETHYLPHENOXYQUINOLINES AND ANALOGUES<br/>[FR] SILYLMÉTHYLPHÉNOXYQUINOLÉINES TRISUBSTITUÉS ET ANALOGUES
  申请人：BAYER AG

  公开号：WO2018202712A1

  公开（公告）日：2018-11-08

  The present disclosure relates to fungicidal active compounds, more specifically to trisubstitutedsilylmethylphenoxyquinolines and analogues thereof, processes and, intermediates for their 5 preparation and use thereof as fungicidal active compound, particularly in the form of fungicide compositions. The present disclosure also relates to methods for the control of phytopathogenic fungi of plants using these compounds or compositions comprising thereof.

  本公开涉及杀真菌活性化合物，更具体地涉及三取代硅甲基苯氧喹啉及其类似物，以及它们的制备过程、中间体和用作杀真菌活性化合物的用途，特别是以杀真菌剂组合物的形式。本公开还涉及使用这些化合物或包含其的组合物控制植物病原真菌的方法。
• [EN] ACTIVE COMPOUND COMBINATIONS<br/>[FR] COMBINAISONS DE COMPOSÉS ACTIFS
  申请人：BAYER AG

  公开号：WO2021239766A1

  公开（公告）日：2021-12-02

  The present invention relates to active compound combinations, in particular within a fungicide composition, which comprise as compound (A) a compound of formula (I) and as compound (B) a further fungicidally active compound as specified below. Moreover, the invention relates to compositions comprising such compound combination and to the use of the compound combinations and the fungicide compositions as biologically active agent, especially for control of phytopathogenic fungi in crop protection and in the protection of industrial materials and as plant growth regulators.

  本发明涉及活性化合物组合，特别是在杀菌剂组合中，其中包括化合物（A）为式（I）的化合物，以及化合物（B）为下文规定的另一种具有杀菌活性的化合物。此外，本发明涉及包含这种化合物组合的组合物以及将这种化合物组合和杀菌剂组合用作生物活性剂的用途，特别是用于控制作物保护中的植物病原真菌和工业材料保护以及作为植物生长调节剂。
• [EN] PYRIDAZINE (THIO)AMIDES AS FUNGICIDAL COMPOUNDS<br/>[FR] PYRIDAZINE (THIO)AMIDES SERVANT DE COMPOSÉS FONGICIDES
  申请人：BAYER AG

  公开号：WO2020109391A1

  公开（公告）日：2020-06-04

  The present disclosure relates to pyridazine (thio)amide compounds, processes and intermediates for their preparation as well as the uses thereof for controlling phytopathogenic microorganisms, such as phytopathogenic fungi.

  本公开涉及吡啶二氮唑（硫）酰胺化合物，它们的制备过程和中间体，以及将其用于控制植物病原微生物（如植物病原真菌）的用途。
• [EN] HETEROCYCLYL PYRIDAZINE AS FUNGICIDAL COMPOUNDS<br/>[FR] HÉTÉROCYCLYL-PYRIDAZINE UTILISÉE EN TANT QUE COMPOSÉS FONGICIDES
  申请人：BAYER AG

  公开号：WO2020127780A1

  公开（公告）日：2020-06-25

  The present disclosure relates to heterocyclyl pyridazine compounds, processes and intermediates for their preparation as well as the uses thereof for controlling phytopathogenic microorganisms, such as phytopathogenic fungi.

  本公开涉及杂环吡啶嘧啶类化合物，它们的制备过程和中间体，以及用途，用于控制植物病原微生物，如植物病原真菌。