3-(苄基氨基)氮杂丁烷-1-羧酸叔丁酯 | 939760-33-5

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物 - 羧酸酯及其衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-(苄基氨基)氮杂丁烷-1-羧酸叔丁酯
• 中文别名: 3-[(苯甲基)氨基]-1-氮杂环丁烷羧酸叔丁酯
• 英文名称: tert-butyl 3-(benzylamino)azetidine-1-carboxylate
• CAS: 939760-33-5
• 化学式: C₁₅H₂₂N₂O₂
• 分子量: 262.352
• InChiKey: ZAAOSMHEKVAPLQ-UHFFFAOYSA-N

物化性质

• 沸点：
  366.1±35.0 °C(Predicted)
• 密度：
  1.10

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  3-(苄基氨基)氮杂丁烷-1-羧酸叔丁酯 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 N-benzyl-N-(3,4-dichlorobenzyl)azetidin-3-amine
  参考文献：
  名称：

  Exploration of 3-Aminoazetidines as Triple Reuptake Inhibitors by Bioisosteric Modification of 3-α-Oxyazetidine

  摘要：

  For a development of broad spectrum antidepressant 3-aminoazetidine derivatives, two series of compounds were explored by bioisosteric modification of 3-α-oxyazetidine. We synthesized 166 novel 3-aminoazetidine derivatives in series A and B, starting from Boc-protected 3-azetidinone (3) and Boc-protected 3-azetidinal (9) respectively, through parallel syntheses. The inhibitory reuptake activities against serotonin (5-HT), norepinephrine (NE), and dopamine (DA) neurotransmitters were measured by the Neurotransmitter Transporter Uptake Assay Kit using the human embryonic kidney 293 (HEK293) cells stably transfected with the respective three kinds of human transporters (hSERT, hNET, and hDAT). Our study aimed to identify compounds having relative inhibitory activities against hSERT > hNET > hDAT. Lead optimization including microsomal stability, CYP, hERG assay, Ames test, BBB, and PK study resulted in the identification of compound 10dl as a candidate for further studies.

  DOI：

  10.1021/ml500187a
• 作为产物：
  描述：

  苄胺 在 sodium tetrahydroborate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 8.0h， 生成 3-(苄基氨基)氮杂丁烷-1-羧酸叔丁酯
  参考文献：
  名称：

  Exploration of 3-Aminoazetidines as Triple Reuptake Inhibitors by Bioisosteric Modification of 3-α-Oxyazetidine

  摘要：

  For a development of broad spectrum antidepressant 3-aminoazetidine derivatives, two series of compounds were explored by bioisosteric modification of 3-α-oxyazetidine. We synthesized 166 novel 3-aminoazetidine derivatives in series A and B, starting from Boc-protected 3-azetidinone (3) and Boc-protected 3-azetidinal (9) respectively, through parallel syntheses. The inhibitory reuptake activities against serotonin (5-HT), norepinephrine (NE), and dopamine (DA) neurotransmitters were measured by the Neurotransmitter Transporter Uptake Assay Kit using the human embryonic kidney 293 (HEK293) cells stably transfected with the respective three kinds of human transporters (hSERT, hNET, and hDAT). Our study aimed to identify compounds having relative inhibitory activities against hSERT > hNET > hDAT. Lead optimization including microsomal stability, CYP, hERG assay, Ames test, BBB, and PK study resulted in the identification of compound 10dl as a candidate for further studies.

  DOI：

  10.1021/ml500187a

文献信息

• [EN] NOVEL N- (4- (AZETIDINE - 1 - CARBONYL) PHENYL) - (HETERO - ) ARYLSULFONAMIDE DERIVATIVES AS PYRUVATE KINASE M2 (PMK2) MODULATORS<br/>[FR] NOUVEAUX DÉRIVÉS DE N-(4-(AZÉTIDINE- 1 - CARBONYL) PHÉNYL)-(HÉTÉRO-) ARYLSULFONAMIDE EN TANT QUE MODULATEURS DE LA PYRUVATE KINASE M2 (PMK2)
  申请人：AGIOS PHARMACEUTICALS INC

  公开号：WO2012083246A1

  公开（公告）日：2012-06-21

  Compounds of general Formula (I), and compositions comprising compounds of general formula I that modulate pyruvate kinase M2 (PKM2) are described herein. Also described herein are methods of using the compounds that modulate PKM2 in the treatment of cancer.

  通用式(I)化合物和包含调节丙酮酸激酶M2（PKM2）的通用式I化合物的组合物在此处进行描述。此外，还描述了利用调节PKM2的化合物治疗癌症的方法。
• Methods of using pyruvate kinase activators
  申请人：Su Shin-San M.

  公开号：US09388164B2

  公开（公告）日：2016-07-12

  Described herein are methods for using compounds that activate pyruvate kinase.

  这里描述了使用激活丙酮酸激酶的化合物的方法。
• METHODS OF USING PYRUVATE KINASE ACTIVATORS
  申请人：Su Shin-San M.

  公开号：US20140155374A1

  公开（公告）日：2014-06-05

  Described herein are methods for using compounds that activate pyruvate kinase.

  本文描述了使用激活丙酮酸激酶的化合物的方法。
• NOVEL N-(4-(AZETIDINE-1-CARBONYL) PHENYL) - (HETERO-) ARYLSULFONAMIDE DERIVATIVES AS PYRUVATE KINASE M2 (PMK2) MODULATORS
  申请人：Salituro Francesco G.

  公开号：US20140073625A1

  公开（公告）日：2014-03-13

  Compounds of general Formula (I), and compositions comprising compounds of general formula I that modulate pyruvate kinase M2 (PKM2) are described herein. Also described herein are methods of using the compounds that modulate PKM2 in the treatment of cancer.

  本文描述了一般式(I)的化合物以及包含该化合物的组合物，这些化合物可以调节丙酮酸激酶M2（PKM2）。本文还描述了使用调节PKM2的化合物治疗癌症的方法。
• N-(4-(azetidine-1-carbonyl) phenyl)-(hetero-) arylsulfonamide derivatives as pyruvate kinase M2 (PMK2) modulators
  申请人：Salituro Francesco G.

  公开号：US09221792B2

  公开（公告）日：2015-12-29

  Compounds of general Formula (I), and compositions comprising compounds of general formula I that modulate pyruvate kinase M2 (PKM2) are described herein. Also described herein are methods of using the compounds that modulate PKM2 in the treatment of cancer.

  本文描述了通式（I）化合物和包含通式（I）化合物的组合物，这些化合物调节丙酮酸激酶M2（PKM2）。本文还描述了使用调节PKM2的化合物治疗癌症的方法。