3-benzyloxycarbonyl-amino-3,4-dihydro-1H-naphthalen-2-one | 132550-75-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-benzyloxycarbonyl-amino-3,4-dihydro-1H-naphthalen-2-one
• 英文别名: 3-benzyloxycarbonylamino-2-oxo-1,2,3,4-tetrahydronaphthalene；benzyl N-(3-oxo-2,4-dihydro-1H-naphthalen-2-yl)carbamate
• CAS: 132550-75-5
• 化学式: C₁₈H₁₇NO₃
• 分子量: 295.338
• InChiKey: IMMSPUFCEPINPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-benzyloxycarbonyl-amino-3,4-dihydro-1H-naphthalen-2-one 在 palladium on activated charcoal 吡啶 、 盐酸 、 氢气 作用下， 以 乙醇 、 水 为溶剂， 生成 3-amino-3,4-dihydro-1H-naphthalen-2-one O-(5-phenylpentyl)oxime hydrochloride
  参考文献：
  名称：

  Synthesis and structure activity relationships of novel non-peptidic metallo-aminopeptidase inhibitors

  摘要：

  Racemic derivatives of 3-amino-2-tetralone were synthesised and evaluated for their ability to inhibit metallo-aminopeptidase activities. New compounds substituted in position 2 by methyl ketone, substituted oximes or hydroxamic acids as well as heterocyclic derivatives were evaluated against representative members of zinc-dependent aminopeptidases: leucine aminopeptidase (E.C. 3.4.11.1), aminopeptidase-N(E.C. 3.4.11.2), Aeronumas proteolytica aminopeptidase (E.C. 3.4.11.10), and the aminopeptidase activity of leukotriene A(4) hydrolase (E.C. 3.3.2.6). Several compounds showed K-i values in the low micromolar range against the 'one-zinc' aminopeptidases, while most of them were rather poor inhibitors of the 'two-zinc' enzymes. This interesting selectivity profile may guide the design of new, specific inhibitors of target mammalian aminopeptidases with one active site zinc. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.06.050
• 作为产物：
  描述：

  2,3-epoxy-1,2,3,4-tetrahydronaphthalene 在 ammonium hydroxide 、 sodium carbonate 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 22.0h， 生成 3-benzyloxycarbonyl-amino-3,4-dihydro-1H-naphthalen-2-one
  参考文献：
  名称：

  Synthesis and structure activity relationships of novel non-peptidic metallo-aminopeptidase inhibitors

  摘要：

  Racemic derivatives of 3-amino-2-tetralone were synthesised and evaluated for their ability to inhibit metallo-aminopeptidase activities. New compounds substituted in position 2 by methyl ketone, substituted oximes or hydroxamic acids as well as heterocyclic derivatives were evaluated against representative members of zinc-dependent aminopeptidases: leucine aminopeptidase (E.C. 3.4.11.1), aminopeptidase-N(E.C. 3.4.11.2), Aeronumas proteolytica aminopeptidase (E.C. 3.4.11.10), and the aminopeptidase activity of leukotriene A(4) hydrolase (E.C. 3.3.2.6). Several compounds showed K-i values in the low micromolar range against the 'one-zinc' aminopeptidases, while most of them were rather poor inhibitors of the 'two-zinc' enzymes. This interesting selectivity profile may guide the design of new, specific inhibitors of target mammalian aminopeptidases with one active site zinc. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.06.050

文献信息

• 2-Amino-3-functionalized tetralin derivatives and related glycogen phosphorylase inhibitors
  申请人：Sher M. Philip

  公开号：US20060111413A1

  公开（公告）日：2006-05-25

  Novel compounds are provided which are glycogen phosphorylase inhibitors which are useful in treating, preventing or slowing the progression of diseases requiring glycogen phosphorylase inhibitor therapy such as diabetes and related conditions (such as hyperglycemia, impaired glucose tolerance, insulin resistance and hyperinsulinemia), the microvascular complications associated with diabetes (such as retinopathy, neuropathy, nephropathy and delayed wound healing), the macrovascular complications associated with diabetes (cardiovascular diseases such as atherosclerosis, abnormal heart function, myocardial ischemia and stroke), as well as Metabolic Syndrome and its component conditions including hypertension, obesity and dislipidemia (including hypertriglyceridemia, hypercholesterolemia and low HDL), and other maladies such as non-cardiac ischemia, infection and cancer. These novel compounds have the structure or stereoisomers or prodrugs or pharmaceutically acceptable salts thereof, wherein W, R 1 , R 2 , X, Y and Z are defined herein.

  提供了新颖的化合物，它们是糖原磷酸化酶抑制剂，可用于治疗、预防或减缓需要糖原磷酸化酶抑制剂治疗的疾病，如糖尿病及相关疾病（如高血糖、糖耐量受损、胰岛素抵抗和高胰岛素血症），与糖尿病相关的微血管并发症（如视网膜病变、神经病变、肾病和伤口愈合延迟）、与糖尿病相关的大血管并发症（心血管疾病，如动脉粥样硬化、心脏功能异常、心肌缺血和中风），以及代谢综合征及其组成疾病，包括高血压、肥胖和脂质代谢异常（包括高三酸甘油酯血症、高胆固醇血症和低HDL），以及其他疾病，如非心脏缺血、感染和癌症。这些新颖的化合物具有特定的结构、立体异构体、前药或其药用可接受的盐，其中W、R1、R2、X、Y和Z在此处被定义。
• US7365061B2
  申请人：——

  公开号：US7365061B2

  公开（公告）日：2008-04-29
• [EN] 2-AMINO-3-FUNCTIONALIZED TETRALIN DERIVATIVES AND RELATED GLYCOGEN PHOSPHORYLASE INHIBITORS<br/>[FR] DERIVES DE 2-AMINO-3-TETRALINE FONCTIONNALISEE ET INHIBITEURS DE LA GLYCOGENE PHOSPHORYLASE ASSOCIES
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2006055463A2

  公开（公告）日：2006-05-26

  [EN] Novel compounds are provided which are glycogen phosphorylase inhibitors which are useful in treating, preventing or slowing the progression of diseases requiring glycogen phosphorylase inhibitor therapy such as diabetes and related conditions (such as hyperglycemia, impaired glucose tolerance, insulin resistance and hyperinsulinemia), the microvascular complications associated with diabetes (such as retinopathy, neuropathy, nephropathy and delayed wound healing), the macrovascular complications associated with diabetes (cardiovascular diseases such as atherosclerosis, abnormal heart function, myocardial ischemia and stroke), as well as Metabolic Syndrome and its component conditions including hypertension, obesity and dislipidemia (including hypertriglyceridemia, hypercholesterolemia and low HDL), and other maladies such as non-cardiac ischemia, infection and cancer. These novel compounds have the structure [INSERT CHEMICAL STRUCTURE HERE] I or stereoisomers or prodrugs or pharmaceutically acceptable salts thereof, wherein W, R1, R2, X and Z are defined herein.
  [FR] L'invention concerne de nouveaux composés inhibiteurs de la glycogène phosphorylase utiles dans le traitement, la prévention ou le ralentissement de l'évolution de maladies nécessitant une thérapie par inhibiteur de le glycogène phosphorylase, telles que les diabètes et des affections associées (telles que l'hyperglicémie, l'altération de la tolérance au glucose, la résistance à l'insuline et l'hyperinsulinémie), les complications microvasculaires associées au diabète (telles que la rétinopathie, la neuropathie, la néphropathie et une cicatrisation retardée), les complications macrovasculaires, telles que l'athérosclérose, une fonction cardiaque anormale, l'ischémie myocardique et l'accident cérébrovasculaire) ainsi que le syndrome métabolique et ses composantes comprenant l'hypertension, l'obésité et la dislipidémie (y compris l'hypertriglycéridémie, l'hypercholestérolémie et une HDL faible) et d'autres maladies telles que l'ischémie non cardiaque, l'infection et le cancer. Ces nouveaux composés ont la structure de formule (I), ou W, R¹, R², X et Z sont définis dans la description. L'invention se rapporte également à des stéréoisomères, des promédicaments ou des sels phramaceutiquement acceptables.