2,2,3,3-Tetramethylcyclopropan-1-amine | 80874-88-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2,2,3,3-Tetramethylcyclopropan-1-amine
• CAS: 80874-88-0
• 化学式: C₇H₁₅N
• mdl: MFCD19215434
• 分子量: 113.203
• InChiKey: KSAYLAYKWFYDET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,2,3,3-Tetramethylcyclopropan-1-amine 、 异硫氰酰甲酸乙酯 以 氯仿 为溶剂， 反应 48.0h， 以380 mg的产率得到1-(2,2,3,3-tetramethylcyclopropyl)thiourea
  参考文献：
  名称：

  2-Amino-1,3-thiazol-4(5H)-ones as Potent and Selective 11β-Hydroxysteroid Dehydrogenase Type 1 Inhibitors: Enzyme−Ligand Co-Crystal Structure and Demonstration of Pharmacodynamic Effects in C57Bl/6 Mice

  摘要：

  11 beta-Hydroxy steroid dehydrogenase type 1 (11 beta-HSD1) has attracted considerable attention during the past few years as a potential target for the treatment of diseases associated with metabolic syndrome. In our ongoing work on 11-HSD1 inhibitors, a series of new 2-amino-1,3-thiazol-4(5H)-ones were explored. By inserting various cycloalkylamines at the 2-position and alkyl groups or spirocycloalkyl groups at the 5-position of the thiazolone, several potent 11 beta-HSD1 inhibitors were identified. An X-ray cocrystal structure of human 11 beta-HSD1 with compound 6d (K-i = 28 nM) revealed a large lipophilic pocket accessible by substitution off the 2-position of the thiazolone. To increase potency, analogues were prepared with larger lipophilic groups at this position. One of these compounds, the 3-noradamantyl analogue 8b, was a potent inhibitor of human 11 beta-HSD 1 (K-i = 3 nM) and also inhibited 11 beta-HSD1 activity in lean C57BI/6 mice when evaluated in an ex vivo adipose and liver cortisone to cortisol conversion assay.

  DOI：

  10.1021/jm701551j
• 作为产物：
  描述：

  2,2,3,3-四甲基环丙甲酸 在 叠氮磷酸二苯酯 、 三乙胺 、 盐酸 作用下， 以 乙腈 、 水 、 氯仿 为溶剂， 反应 7.0h， 生成 2,2,3,3-Tetramethylcyclopropan-1-amine
  参考文献：
  名称：

  2-Amino-1,3-thiazol-4(5H)-ones as Potent and Selective 11β-Hydroxysteroid Dehydrogenase Type 1 Inhibitors: Enzyme−Ligand Co-Crystal Structure and Demonstration of Pharmacodynamic Effects in C57Bl/6 Mice

  摘要：

  11 beta-Hydroxy steroid dehydrogenase type 1 (11 beta-HSD1) has attracted considerable attention during the past few years as a potential target for the treatment of diseases associated with metabolic syndrome. In our ongoing work on 11-HSD1 inhibitors, a series of new 2-amino-1,3-thiazol-4(5H)-ones were explored. By inserting various cycloalkylamines at the 2-position and alkyl groups or spirocycloalkyl groups at the 5-position of the thiazolone, several potent 11 beta-HSD1 inhibitors were identified. An X-ray cocrystal structure of human 11 beta-HSD1 with compound 6d (K-i = 28 nM) revealed a large lipophilic pocket accessible by substitution off the 2-position of the thiazolone. To increase potency, analogues were prepared with larger lipophilic groups at this position. One of these compounds, the 3-noradamantyl analogue 8b, was a potent inhibitor of human 11 beta-HSD 1 (K-i = 3 nM) and also inhibited 11 beta-HSD1 activity in lean C57BI/6 mice when evaluated in an ex vivo adipose and liver cortisone to cortisol conversion assay.

  DOI：

  10.1021/jm701551j

文献信息

• Branched amides of L-aspartyl-D-amino acid dipeptides and compositions thereof
  申请人：PFIZER INC.

  公开号：EP0034876A2

  公开（公告）日：1981-09-02

  Amides of L-aspartyl-D-amino acid dipeptides of the formula and physiologically acceptable cationic and acid addition salts thereof wherein Ra is methyl, ethyl, n-propyl or isopropyl and R is a branched aliphatic, alicyclic or heterocyclic member which is branched at the alpha carbon atom (the carbon atom bearing the amide nitrogen atom) and also branched again at one or both of the beta carbon atoms, are potent sweeteners which are free from undesirable flavour qualities and of high stability in conventional food processing. Sweetening compositions and sweetened edible compositions of such amides are also claimed

  式中 L-天冬氨酰-D-氨基酸二肽的酰胺类 及其生理上可接受的阳离子盐和酸加成盐，其中 Ra 为甲基、乙基、正丙基或异丙基，R 为支链脂环族、脂环族或杂环族成员，该成员在 α 碳原子（含酰胺氮原子的碳原子）上有支链，在一个或两个β碳原子上也有支链。这种酰胺的甜味组合物和甜味可食用组合物也已申请专利。
• BRENNAN, THOMAS M.;HENDRICK, MICHAEL E.
  作者：BRENNAN, THOMAS M.、HENDRICK, MICHAEL E.

  DOI：——

  日期：——
• BRENNAN, T. M.;EZELL, H. M.
  作者：BRENNAN, T. M.、EZELL, H. M.

  DOI：——

  日期：——
• BRENNAN, THOMAS M.;HENDRICK, MICHAEL F.
  作者：BRENNAN, THOMAS M.、HENDRICK, MICHAEL F.

  DOI：——

  日期：——
• US4399163A
  申请人：——

  公开号：US4399163A

  公开（公告）日：1983-08-16