DL-3-氨基-3-(2-甲氧基苯基)丙酸 | 103095-63-2

• 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
• 中文名称: DL-3-氨基-3-(2-甲氧基苯基)丙酸
• 中文别名: (RS)-3-氨基-3-(2-甲氧基苯基)丙酸；3-氨基-3-(2-甲氧基苯基)丙酸
• 英文名称: 3-amino-3-(2-methoxy-phenyl)-propionic acid
• 英文别名: 3-Amino-3-(2-methoxy-phenyl)-propionsaeure；β-Amino-2-methoxy-hydrozimtsaeure；β-Amino-β-(2-methoxy-phenyl)-propionsaeure；3-amino-3-(2-methoxyphenyl)propionic acid；3-azaniumyl-3-(2-methoxyphenyl)propanoate
• CAS: 103095-63-2
• 化学式: C₁₀H₁₃NO₃
• 分子量: 195.218
• InChiKey: UAZGIQATDPCZHH-UHFFFAOYSA-N

物化性质

• 熔点：
  209-210 °C (decomp)
• 沸点：
  360.5±37.0 °C(Predicted)
• 密度：
  1.206±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  72.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2922509090
• 危险类别：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  DL-3-氨基-3-(2-甲氧基苯基)丙酸 在 盐酸 、 氯化亚砜 、 异丁基硼酸 、 水 、 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 、 N,N'-二环己基碳二亚胺 、 sodium hydroxide 作用下， 以 甲醇 、 四氯化碳 、 正己烷 、 二氯甲烷 、 水 、 丙酮 为溶剂， 生成 (R)-1-[3-benzamido-3-(2-methoxyphenyl)propanamido]-3-methylbutylboronic acid
  参考文献：
  名称：

  Synthesis, in Vitro and in Vivo Biological Evaluation, and Comprehensive Understanding of Structure−Activity Relationships of Dipeptidyl Boronic Acid Proteasome Inhibitors Constructed from β-Amino Acids

  摘要：

  An extensive structure-activity relationship (SAR) study of 72 dipeptidyl boronic acid proteasome inhibitors constructed from beta-amino acids is reported. SAR analysis revealed that bicyclic groups at the RI position, 3-F substituents at the R-2 position, and bulky aliphatic groups at the R-3 position were favorable to the activities. Enzymatic screening results showed that compound 78, comprising all of these features, was the most active inhibitor against the 20S human proteasome at less than a 2 nM level, as active as the marketed drug bortezomib. Cellular assays confirmed that compound 78 was the most potent against two hematologic and some solid tumor cells with IC50 values less than 1 mu M. Pharmacokinetic profiles suggested that 78 showed higher plasma exposure and a longer half-life than bortezomib.

  DOI：

  10.1021/jm1009742
• 作为产物：
  描述：

  2-甲氧基肉桂酸 在 palladium on activated charcoal 盐酸羟胺 、 氢气 、 sodium acetate 作用下， 以 乙醇 为溶剂， 生成 DL-3-氨基-3-(2-甲氧基苯基)丙酸
  参考文献：
  名称：

  Basheeruddin,K. et al., Synthetic Communications, 1979, vol. 9, p. 705 - 712

  摘要：

  DOI：

文献信息

• Imides
  申请人：Celgene Corporation

  公开号：US05605914A1

  公开（公告）日：1997-02-25

  Cyclic imides are inhibitors of tumor necrosis factor .alpha. and can be used to combat cachexia, endotoxic shock, and retrovirus replication. A typical embodiment is 2-(2,6-dioxo-3-piperidinyl)-4-azaisoindoline-1,3-dione.

  环酰亚胺是肿瘤坏死因子α的抑制剂，可用于对抗消瘦症、内毒素休克和逆转录病毒复制。一个典型的实施例是2-(2,6-二氧代-3-哌啶基)-4-氮杂异吲哚-1,3-二酮。
• Cyclic amides
  申请人：Celgene Corporation

  公开号：US05698579A1

  公开（公告）日：1997-12-16

  Cyclic amides are inhibitors of tumor necrosis factor and can be used to combat cachexia, endotoxic shock, and retrovirus replication. A typical embodiment is 3-phenyl-3-(1-oxoisoindolin-2-yl)propionamide.

  环酰胺是肿瘤坏死因子的抑制剂，可用于对抗消瘦症、内毒素休克和逆转录病毒复制。一个典型的实施例是3-苯基-3-(1-氧代异吲哚啉-2-基)丙酰胺。
• Ring closure of N-phthaloylglutamines
  申请人：Celgene Corporation

  公开号：US05463063A1

  公开（公告）日：1995-10-31

  Cyclic imides are inhibitors of tumor necrosis factor .alpha. and can be used to combat cachexia, endotoxic shock, and retrovirus replication. A typical embodiment is 2-(2,6-dioxo-3-piperidinyl)-4-azaisoindoline-1,3-dione.

  环酰亚胺是肿瘤坏死因子α的抑制剂，可用于对抗消瘦症、内毒素休克和逆转录病毒复制。一个典型的实施例是2-(2,6-二氧代-3-哌啶基)-4-氮杂异吲哚-1,3-二酮。
• [EN] THIAZOLIDINE CARBOXAMIDE DERIVATIVES AS MODULATORS OF THE PROSTAGLANDIN F RECEPTOR<br/>[FR] DERIVES DE THIAZOLIDINE CARBOXAMIDE UTILES EN TANT QUE MODULATEURS DU RECEPTEUR DE PROSTAGLANDINE F
  申请人：APPLIED RESEARCH SYSTEMS

  公开号：WO2003082278A1

  公开（公告）日：2003-10-09

  The present invention is related to thiazolidine carboxamide derivatives of formula (II) for the treatment and/or prophylaxis of preterm labor, premature birth, dysmenorrhea and for stopping labor prior to cesarean delivery. G is selected from the group consisting of C1-C6-alkyl aryl, C1-C6-alkyl heteroaryl, C1-C6 Alkyl cycloalkyl, C1-C6-alkyl heteroaryl, aryl, heteroaryl, C3-C8-cycloalkyl or -heterocyclo­alkyl, said cycloalkyl or aryl or heteroaryl groups may be fused with cycloalkyl or aryl or heteroaryl groups. R1 is selected from the group consisting of aryl, heteroaryl, C3-C8-cycloalkyl or - heterocyclo-alkyl, said (hetero)cycloalkyl or aryl or heteroaryl groups may be fused with (hetero)cycloalkyl or aryl or heteroaryl groups. R2 is selected from the group consisting of H, carboxy, acyl, alkoxycarbonyl, amino­carbonyl, C1-C5-alkyl carboxy, C1-C5-alkyl acyl, C1-C5-alkyl alkoxycarbonyl, C1-C5-alkyl aminocarbonyl, C1-C5-alkyl acyloxy, C1-C5-alkyl acylamino, C1 -C5-alkyl ureido, C1-C5alkyl amino, C1-C5-alkyl alkoxy, C1-C5-alkyl sulfanyl, C1-C5-alkyl sulfinyl, C1-C5-alkyl sulfonyl, C1-C5-alkyl sulfonylamino, C1-C5-alkyl sulfonyloxy, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, aryl, heteroaryl, C3-C8-cycloalkyl, heterocycloalkyl, C1-C6-alkyl aryl, C2-C6-alkyl heteroaryl, C1-C6-alkyl cycloalkyl, C1-C6-alkyl heterocycloalkyl, C2-C6-alkenyl aryl, C2-C6-alkenyl heteroaryl, C2-C6-alkynyl aryl, or C2-C6-alkynyl heteroaryl.

  本发明涉及公式（II）的噻唑烷羧酰胺衍生物，用于治疗和/或预防早产、早产、痛经以及在剖腹产前停止分娩。G选自C1-C6烷基芳基、C1-C6烷基杂芳基、C1-C6烷基环烷基、C1-C6烷基杂芳基、芳基、杂芳基、C3-C8环烷基或-杂环烷基，所述环烷基或芳基或杂芳基基团可能与环烷基或芳基或杂芳基基团融合。R1选自芳基、杂芳基、C3-C8环烷基或-杂环烷基，所述（杂）环烷基或芳基或杂芳基基团可能与（杂）环烷基或芳基或杂芳基基团融合。R2选自H、羧基、酰基、烷氧羰基、氨基羰基、C1-C5烷基羧基、C1-C5烷基酰基、C1-C5烷基烷氧羰基、C1-C5烷基氨基羰基、C1-C5烷基酰氧基、C1-C5烷基酰胺基、C1-C5烷基脲基、C1-C5烷基氨基、C1-C5烷基烷氧基、C1-C5烷基硫醇基、C1-C5烷基亚砜基、C1-C5烷基磺酰基、C1-C5烷基磺酰胺基、C1-C5烷基磺酰氧基、C1-C6烷基、C2-C6烯基、C2-C6炔基、芳基、杂芳基、C3-C8环烷基、杂环烷基、C1-C6烷基芳基、C2-C6烷基杂芳基、C1-C6烷基环烷基、C1-C6烷基杂环烷基、C2-C6烯基芳基、C2-C6烯基杂芳基、C2-C6炔基芳基或C2-C6炔基杂芳基。
• 3-Amino-3-arylpropionic acid n-alkyl esters, process for production thereof, and process for production of optically active 3-amino-3-arylpropionic acids and esters of the antipodes thereto
  申请人：Yamamoto Yasuhito

  公开号：US20060178433A1

  公开（公告）日：2006-08-10

  The present invention is to provide an n-alkyl 3-amino-3-arylpropionate represented by the formula (I): wherein Ar 1 represents an aryl group which may have a substituent(s), provided that a phenyl group and 4-methoxyphenyl group are excluded, R 1 represents an n-propyl group or an n-butyl group, and a process for preparing the same, and its optically active compound and an optically active (S or R)-3-amino-3-arylpropionic acid represented by the formula (III-a): wherein Ar represents an aryl group which may have a substituent(s), and * represents an asymmetric carbon, and a process for preparing an optically active n-alkyl (R or S)-3-amino-3-arylpropionate represented by the formula (IV-a): wherein Ar and R 1 have the same meanings as defined above, * represents an asymmetric carbon, provided that it has a reverse absolute configuration to the compound of the formula (III-a).

  本发明提供了一种n-烷基3-氨基-3-芳基丙酸酯，其化学式表示为(I)：其中，Ar1表示一个芳基基团，可以具有一个或多个取代基，但不包括苯基和4-甲氧基苯基；R1表示一个n-丙基基团或n-丁基基团。本发明还提供了制备该化合物的方法，以及其光学活性化合物和光学活性(S或R)-3-氨基-3-芳基丙酸的化学式表示为(III-a)：其中，Ar表示一个芳基基团，可以具有一个或多个取代基，*表示一个不对称碳，以及制备光学活性n-烷基(R或S)-3-氨基-3-芳基丙酸酯的方法，其化学式表示为(IV-a)：其中，Ar和R1的含义与上述定义相同，*表示一个不对称碳，但其绝对构型与化合物的化学式(III-a)相反。