1-(aminomethyl)cyclobutanecarboxylic acid methyl ester | 1027337-70-7

• 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: 1-(aminomethyl)cyclobutanecarboxylic acid methyl ester
• 英文别名: Methyl 1-(Aminomethyl)cyclobutanecarboxylate；methyl 1-(aminomethyl)cyclobutane-1-carboxylate
• CAS: 1027337-70-7
• 化学式: C₇H₁₃NO₂
• 分子量: 143.186
• InChiKey: BOOWYKHRIQPXJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(aminomethyl)cyclobutanecarboxylic acid methyl ester 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 1-(aminomethyl)cyclobutanecarboxylic acid
  参考文献：
  名称：

  Preparation and Structure ofβ-Peptides Consisting of Geminally Disubstitutedβ2,2- andβ3,3-Amino Acids: A Turn Motif forβ-Peptides

  摘要：

  We report on the synthesis of new and previously described beta-peptides (1-6), consisting of up to twelve beta(2,2-) or beta(3,3)-geminally disubstituted beta-amino acids which do not fit into any of the secondary structural patterns of beta-peptides, hitherto disclosed. The required 2,2- and 3,3-dimethyl derivatives of 3-aminopropanoic acid are readily obtained from 3-methylbut-2-enoic acid and ammonia (Scheme 1) and from Boc-protected methyl 3-aminopropanoate by enolate methylation (Scheme 2). Protected (Boc for solution-, Fmoc for solid-phase syntheses) 1-(aminomethyl)cycloalkanecarboxylic-acid derivatives (with cyclopropane, cyclobutane, cyclopentane, and cyclohexane rings) are obtained from 1-cyanocycloalkanecarboxylates and the corresponding dihaloalkanes (Scheme 3). Fully C-13- and N-15-labeled 3-amino-2,2-dimethylpropanoic-acid derivatives were prepared from the corresponding labeled precursors (see asterixed formula numbers and Scheme 4). Coupling of these amino acids was achieved by methods which we had previously employed for other beta-peptide syntheses ( intermediates 18 - 23). Crystal structures of Boc-protected geminally disubstituted amine acids (16a-d) and of the corresponding tripeptide (23a), as well as NMR and IR spectra of an isotopically labeled beta-hexapeptide (2a*) are presented (Figs. 1-4) and discussed. The tripeptide structure contains a ten-membered H-bonded ring which is proposed to be a turn-forming motif for beta-peptides (Fig. 2).

  DOI：

  10.1002/(sici)1522-2675(19981216)81:12<2218::aid-hlca2218>3.0.co;2-0
• 作为产物：
  描述：

  1-氰基环丁烷羧酸甲酯 在 镍 氢气 作用下， 以 甲醇 为溶剂， 40.0 ℃ 、400.0 kPa 条件下， 反应 22.0h， 生成 1-(aminomethyl)cyclobutanecarboxylic acid methyl ester
  参考文献：
  名称：

  Preparation and Structure ofβ-Peptides Consisting of Geminally Disubstitutedβ2,2- andβ3,3-Amino Acids: A Turn Motif forβ-Peptides

  摘要：

  We report on the synthesis of new and previously described beta-peptides (1-6), consisting of up to twelve beta(2,2-) or beta(3,3)-geminally disubstituted beta-amino acids which do not fit into any of the secondary structural patterns of beta-peptides, hitherto disclosed. The required 2,2- and 3,3-dimethyl derivatives of 3-aminopropanoic acid are readily obtained from 3-methylbut-2-enoic acid and ammonia (Scheme 1) and from Boc-protected methyl 3-aminopropanoate by enolate methylation (Scheme 2). Protected (Boc for solution-, Fmoc for solid-phase syntheses) 1-(aminomethyl)cycloalkanecarboxylic-acid derivatives (with cyclopropane, cyclobutane, cyclopentane, and cyclohexane rings) are obtained from 1-cyanocycloalkanecarboxylates and the corresponding dihaloalkanes (Scheme 3). Fully C-13- and N-15-labeled 3-amino-2,2-dimethylpropanoic-acid derivatives were prepared from the corresponding labeled precursors (see asterixed formula numbers and Scheme 4). Coupling of these amino acids was achieved by methods which we had previously employed for other beta-peptide syntheses ( intermediates 18 - 23). Crystal structures of Boc-protected geminally disubstituted amine acids (16a-d) and of the corresponding tripeptide (23a), as well as NMR and IR spectra of an isotopically labeled beta-hexapeptide (2a*) are presented (Figs. 1-4) and discussed. The tripeptide structure contains a ten-membered H-bonded ring which is proposed to be a turn-forming motif for beta-peptides (Fig. 2).

  DOI：

  10.1002/(sici)1522-2675(19981216)81:12<2218::aid-hlca2218>3.0.co;2-0

文献信息

• [EN] 4 -HYDROXY- ISOQUINOLINE COMPOUNDS AS HIF HYDROXYLASE INHIBITORS<br/>[FR] COMPOSÉS 4-HYDROXY-ISOQUINOLÉINE COMME INHIBITEURS D'HYDROXYLASE HIF
  申请人：FIBROGEN INC

  公开号：WO2013134660A1

  公开（公告）日：2013-09-12

  The present invention relates to novel compounds of formula (I), and compositions capable of inhibiting PHD1 enzyme activity selectively over other isoforms, for example, PHD2 and/or PHD3 enzymes. The invention also relates to compounds of formula (I) for use in disorders such as muscle degeneration, colitis, IBD, and certain ischemias.

  本发明涉及式(I)的新化合物，以及能够选择性地抑制PHD1酶活性而不影响其他同工酶（例如PHD2和/或PHD3酶）的组合物。该发明还涉及式(I)的化合物在肌肉退化、结肠炎、炎症性肠病和某些缺血症等疾病中的应用。
• [EN] 7- OR 8-HYDROXY-ISOQUINOLINE AND 7- OR 8-HYDROXY-QUINOLINE DERIVATIVES AS ALPHA-1 -ANTITRYPSIN MODULATORS FOR TREATING ALPHA-1 -ANTITRYPSIN DEFICIENCY (AATD)<br/>[FR] DÉRIVÉS DE 7-OU 8-HYDROXY-ISOQUINOLÉINE ET DE 7-OU 8-HYDROXY-QUINOLÉINE EN TANT QUE MODULATEURS D'ALPHA-1-ANTITRYPSINE POUR TRAITER UNE DÉFICIENCE EN ALPHA-1-ANTITRYPSINE (AATD)
  申请人：VERTEX PHARMA

  公开号：WO2021203028A1

  公开（公告）日：2021-10-07

  7- or 8-hydroxy-isoquinoline and 7- or 8-hydroxy-quinoline derivatives as alpha-l-antitrypsin modulators for treating alpha-l-antitrypsin deficiency (AATD).

  7-或8-羟基异喹啉和7-或8-羟基喹啉衍生物作为治疗α-1-抗胰蛋白酶缺乏症（AATD）的α-1-抗胰蛋白酶调节剂。
• [EN] PYRIMIDINE DERIVATIVES AS PROTEIN KINASE INHIBITORS<br/>[FR] DÉRIVÉS DE PYRIMIDINE COMME INHIBITEURS DE PROTÉINE KINASES
  申请人：CYCLACEL LTD

  公开号：WO2009040556A1

  公开（公告）日：2009-04-02

  The present invention relates to a compound of formula (VII)I, or a pharmaceutically acceptable salt or ester thereof, wherein: X is NR7; Y is O or N-(CH2)nR19; n is 1, 2 or 3; m is 1 or 2; R1 and R2 are each independently H, alkyl or cycloalkyl; R4 and R4' are each independently H or alkyl; or R4 and R4' together form a spiro cycloalkyl group; R19 is H, alkyl, aryl or a cycloalkyl group; R6 is OR8 or halogen; and R7 and R8 are each independently H or alkyl. Further aspects relate to pharmaceutical compositions comprising said compounds and use therefore in the treatment of proliferative disorders and the like.

  本发明涉及公式(VII)I的化合物，或其药学上可接受的盐或酯，其中：X为NR7；Y为O或N-(CH2)nR19；n为1、2或3；m为1或2；R1和R2分别独立地为H、烷基或环烷基；R4和R4'分别独立地为H或烷基；或者R4和R4'一起形成螺环烷基基团；R19为H、烷基、芳基或环烷基基团；R6为OR8或卤素；而R7和R8各自独立地为H或烷基。进一步方面涉及包括上述化合物的药物组合物以及其在治疗增殖性疾病等方面的用途。
• BICYCLIC CX3CR1 RECEPTOR AGONISTS
  申请人：Board of Regents, The University of Texas System

  公开号：US20210024510A1

  公开（公告）日：2021-01-28

  Disclosed herein are novel cycloalka[b]heteroaryl compounds having CX3CR1/fractalkine receptor (CX3CR1) agonistic properties, pharmaceutical compositions comprising these compounds, chemical processes for preparing these compounds and their use in the treatment or prophylaxis of diseases associated with CX3CR1 receptor activity in animals, in particular humans.

  本文披露了一种新颖的环烷基[b]杂环芳烃化合物，具有CX3CR1/趋化因子受体（CX3CR1）激动性特性，包括这些化合物的药物组合物，制备这些化合物的化学过程以及它们在治疗或预防与动物中的CX3CR1受体活性相关的疾病，尤其是人类中的用途。
• PYRIMIDINE DERIVATIVES AS PROTEIN KINASE INHIBITORS
  申请人：Hollick Jonathan James

  公开号：US20110046093A1

  公开（公告）日：2011-02-24

  The present invention relates to a compound of formula (VII)I, or a pharmaceutically acceptable salt or ester thereof, wherein: X is NR 7 ; Y is O or N—(CH 2 ) n R 19 ; n is 1, 2 or 3; m is 1 or 2; R 1 and R 2 are each independently H, alkyl or cycloalkyl; R 4 and R 4′ each independently H alkyl; or R 4 and R 4′ together form a spiro cycloalkyl group; R 19 is H, alkyl, aryl or a cycloalkyl group; R 6 is OR 8 or halogen; and R 7 and R 8 are each independently H or alkyl. Further aspects relate to pharmaceutical compositions comprising said compounds and use therefore in the treatment of proliferative disorders and the like.

  本发明涉及一种化合物，其化学式为(VII)I，或其药学上可接受的盐或酯，其中：X为NR7；Y为O或N-(CH2)nR19；n为1、2或3；m为1或2；R1和R2各自独立地为H、烷基或环烷基；R4和R4′各自独立地为H烷基；或R4和R4′共同形成一个螺环烷基；R19为H、烷基、芳基或环烷基；R6为OR8或卤素；R7和R8各自独立地为H或烷基。此外，该发明还涉及包含上述化合物的制药组合物以及其在治疗增生性疾病等方面的用途。