1-(S)-amino-4-methylindan-5-carboxylic acid tert-butyl ester | 903557-93-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 1-(S)-amino-4-methylindan-5-carboxylic acid tert-butyl ester
• 英文别名: (S)-1-amino-4-methyl-indan-5-carboxylic acid tert-butyl ester；(1S)-1-amino-4-methylindan-5-carboxylic acid tert-butyl ester；(S)-tert-butyl 1-amino-4-methyl-2,3-dihydro-1H-indene-5-carboxylate；tert-butyl (1S)-1-amino-4-methyl-2,3-dihydro-1H-indene-5-carboxylate
• CAS: 903557-93-7
• 化学式: C₁₅H₂₁NO₂
• 分子量: 247.337
• InChiKey: LLSUNXRXXMMHGQ-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 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-(S)-amino-4-methylindan-5-carboxylic acid tert-butyl ester 在 N-甲基吗啉 、 bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以48%的产率得到methyl 6-[[(1S)-4-methyl-5-[(2-methylpropan-2-yl)oxycarbonyl]-2,3-dihydro-1H-inden-1-yl]carbamoyl]pyrimidine-4-carboxylate
  参考文献：
  名称：

  Metalloprotease inhibitors

  摘要：

  本发明涉及具有含芳香族MMP抑制化合物的酰胺，其具有单酰胺杂芳基团，化学式I和II：

  公开号：

  US20080021024A1
• 作为产物：
  描述：

  tert-butyl (1S)-4-methyl-1-[(2-methylpropan-2-yl)oxycarbonylamino]-2,3-dihydro-1H-indene-5-carboxylate 在 硫酸 、 水 、 碳酸氢钠 作用下， 以 醋酸叔丁酯 、 乙酸乙酯 为溶剂， 反应 5.0h， 以99%的产率得到1-(S)-amino-4-methylindan-5-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Metalloprotease inhibitors

  摘要：

  本发明涉及具有含芳香族MMP抑制化合物的酰胺，其具有单酰胺杂芳基团，化学式I和II：

  公开号：

  US20080021024A1

文献信息

• Multicyclic bis-amide MMP inhibitors
  申请人：Powers Timothy

  公开号：US20060173183A1

  公开（公告）日：2006-08-03

  The present invention relates generally to bis-amide group containing pharmaceutical agents, and in particular, to multicyclic bis-amide MMP-13 inhibitor compounds. More particularly, the present invention provides a new class of MMP-13 inhibiting compounds, containing a pyrimidinyl bis-amide group in combination with a heterocyclic moiety, that exhibit an increased potency and solubility in relation to currently known bis-amide group containing MMP-13 inhibitors.

  本发明总体涉及含有双酰胺基团的药物制剂，特别是多环双酰胺MMP-13抑制剂化合物。更具体地，本发明提供了一类新型的MMP-13抑制化合物，它们含有与杂环部分结合的嘧啶基双酰胺基团，与目前已知含双酰胺基团的MMP-13抑制剂相比，显示出增加的活性和溶解度。
• Heterobicyclic metalloprotease inhibitors
  申请人：Gallagher M. Brian

  公开号：US20070155737A1

  公开（公告）日：2007-07-05

  The present invention relates generally to amide group containing pharmaceutical agents, and in particular, to amide containing heterobicyclic metalloprotease inhibitor compounds. More particularly, the present invention provides a new class of heterobicyclic ADAMTS-4 inhibiting compounds.

  本发明通常涉及含有酰胺基团的药物，特别是含有酰胺基团的杂双环金属蛋白酶抑制剂化合物。更具体地，本发明提供了一类新的杂双环ADAMTS-4抑制剂化合物。
• WO2006/128184
  申请人：——

  公开号：——

  公开（公告）日：——
• Discovery and Evaluation of a Non-Zn Chelating, Selective Matrix Metalloproteinase 13 (MMP-13) Inhibitor for Potential Intra-articular Treatment of Osteoarthritis
  作者：Christian Gege、Bagna Bao、Harald Bluhm、Jürgen Boer、Brian M. Gallagher、Brian Korniski、Timothy S. Powers、Christoph Steeneck、Arthur G. Taveras、Vijaykumar M. Baragi

  DOI：10.1021/jm201152u

  日期：2012.1.26

  Osteoarthritis (OA) is a nonsystemic disease for which no oral or parenteral disease-modifying osteoarthritic drug (DMOAD) is currently available. Matrix metalloproteinase 13 (MMP-13) has attracted attention as a target with disease-modifying potential because of its major role in tissue destruction associated with OA. Being localized to one or a few joints, OA is amenable to intra-articular (IA) therapy, which has distinct advantages over oral therapies in terms of increasing therapeutic index, by maximizing drug delivery to cartilage and minimizing systemic exposure. Here we report on the synthesis and biological evaluation of a non-zinc binding MMP-13 selective inhibitor, 4-methyl-1-(S)-(5-[(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethyl)carbamoyl]pyrazolo[1,5-a]pyrimidine-7-carbonyl}amino)indan-5-carboxylic acid (1), that is uniquely suited as a potential IA-DMOAD: it has long durability in the joint, penetrates cartilage effectively, exhibits nearly no detectable systemic exposure, and has remarkable efficacy.
• HETEROBICYLIC METALLOPROTEASE INHIBITORS
  申请人：Alantos Pharmaceuticals, Inc.

  公开号：EP2038284A2

  公开（公告）日：2009-03-25