[1,2,5]triazepane-1-carboxylic acid tert-butyl ester | 1138150-46-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: [1,2,5]triazepane-1-carboxylic acid tert-butyl ester
• 英文别名: [1,2,5]triazepane-1-carboxylic acid t-butyl ester；Tert-butyl 1,2,5-triazepane-1-carboxylate
• CAS: 1138150-46-5
• 化学式: C₉H₁₉N₃O₂
• 分子量: 201.269
• InChiKey: JJFSNPFPUKXQID-UHFFFAOYSA-N

物化性质

• 沸点：
  271.9±50.0 °C(Predicted)
• 密度：
  1.034±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  53.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [1,2,5]triazepane-1-carboxylic acid tert-butyl ester 在 正丁基锂 、 sodium azide 、 palladium 10% on activated carbon 、 氢气 、 sodium carbonate 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， -78.0~90.0 ℃ 、101.33 kPa 条件下， 反应 108.01h， 生成 5(S)-(thioacetylaminomethyl)-3-(3-fluoro-4-(1-(tertbutoxycarbonyl)[1,2,5]triazepan-5-yl)phenyl)oxazolidin-2-one
  参考文献：
  名称：

  Antibacterial oxazolidinone analogues having a N-hydroxyacetyl-substituted seven-membered [1,2,5]triazepane or [1,2,5]oxadiazepane C-ring unit

  摘要：

  We synthesized a series of oxazolidinone analogues bearing a N-hydroxyacetyl-substituted [1,2,5]triazepane or [1,2,5]oxadiazepane C-ring unit as homologues of an earlier drug candidate, eperezolid. Several of these compounds exhibited potent in vitro antibacterial activities towards not only Gram-positive, but also Gram-negative and linezolid-resistant pathogens. Compounds 21a and 21b, bearing a thiocarbamate side chain, showed high in vivo activity against methicillin-resistant Staphylococcus aureus SR3637, together with a promising safety profile in terms of weak inhibition of monoamine oxidase and cytochrome P450 isozymes. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.03.003
• 作为产物：
  描述：

  1-O,5-O-dibenzyl 2-O-tert-butyl 1,2,5-triazepane-1,2,5-tricarboxylate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 生成 [1,2,5]triazepane-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis and Application of [1,2,5]Triazepane and [1,2,5]Oxadiazepane as Versatile Structural Units for Drug Discovery

  摘要：

  合成了七元杂环 [1,2,5] 三氮杂平和 [1,2,5] 氧杂二氮平衍生物，作为药物发现中替代传统哌嗪或吗啉的候选结构，提供了多个功能团修饰位点。我们首先合成了N保护的杂环，然后通过合成抗菌药物氟氯西林的类似物来验证其有效性。这些类似物表现出强大的体外和体内抗菌活性。特别是化合物10a在小鼠模型中采用静脉注射时，对抗耐甲氧西林金黄色葡萄球菌SR3637表现出良好的体内疗效。这些七元杂环有望成为药物发现中多功能的结构单元。

  DOI：

  10.1248/cpb.58.1001

文献信息

• OXAZOLIDINONE DERIVATIVE HAVING 7-MEMBERED HETERO RING
  申请人：Suzuki Hideyuki

  公开号：US20100256355A1

  公开（公告）日：2010-10-07

  The present invention provides a novel oxazolidinone derivative of the formula (I): wherein Ring A is (A-1) a 7-membered monocyclic heterocycle containing three N atoms; (A-2) a 7-membered monocyclic heterocycle containing two N atoms and one O atom; or (A-3) a 7-membered monocyclic heterocycle containing two N atoms and one S atom, SO or SO 2 , wherein said monocyclic heterocycle is optionally substituted, optionally unsaturated and optionally fused with another ring; X 1 is a single bond, or a heteroatom-containing group selected from the group consisting of —O—, —S—, —NR 2 —, —CO—, —CS—, —CONR 3 —, —NR 4 CO—, —SO 2 NR 5 —, and —NR 6 SO 2 —, wherein R 2 , R 3 , R 4 , R 5 and R 6 are independently hydrogen or lower alkyl, or lower alkylene or lower alkenylene each optionally interrupted by said heteroatom-containing group; Ring B is optionally substituted carbocycle or optionally substituted heterocycle; and R 1 is hydrogen, or an organic residue which is able to bind to the 5 -position of the oxazolidinone ring in oxazolidinone antimicrobial agents, pharmaceutically acceptable salts and solvates thereof which are useful as an antibacterial agent.
• US8530646B2
  申请人：——

  公开号：US8530646B2

  公开（公告）日：2013-09-10
• Antibacterial oxazolidinone analogues having a N-hydroxyacetyl-substituted seven-membered [1,2,5]triazepane or [1,2,5]oxadiazepane C-ring unit
  作者：Hideyuki Suzuki、Iwao Utsunomiya、Koichi Shudo、Norio Fukuhara、Tsutomu Iwaki、Tatsuro Yasukata

  DOI：10.1016/j.ejmech.2013.03.003

  日期：2013.5

  We synthesized a series of oxazolidinone analogues bearing a N-hydroxyacetyl-substituted [1,2,5]triazepane or [1,2,5]oxadiazepane C-ring unit as homologues of an earlier drug candidate, eperezolid. Several of these compounds exhibited potent in vitro antibacterial activities towards not only Gram-positive, but also Gram-negative and linezolid-resistant pathogens. Compounds 21a and 21b, bearing a thiocarbamate side chain, showed high in vivo activity against methicillin-resistant Staphylococcus aureus SR3637, together with a promising safety profile in terms of weak inhibition of monoamine oxidase and cytochrome P450 isozymes. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Synthesis and Application of [1,2,5]Triazepane and [1,2,5]Oxadiazepane as Versatile Structural Units for Drug Discovery
  作者：Hideyuki Suzuki、Iwao Utsunomiya、Koichi Shudo

  DOI：10.1248/cpb.58.1001

  日期：——

  Seven-membered heterocyclic [1,2,5]triazepane and [1,2,5]oxadiazepane derivatives were synthesized as candidate structures for application in drug discovery in place of conventional piperazine or morpholine moieties, offering multiple sites for modification with functional groups. We first synthesized the N-protected heterocycles, and then confirmed their utility by synthesizing analogues of the oxazolidinone antibacterial agent linezolid. The analogues exhibited potent in vitro and in vivo antibacterial activity. In particular, compound 10a exhibited good in vivo efficacy when administered intravenously in a murine model of systemic infection with methicillin-resistant Staphylococcus aureus SR3637. These seven-membered heterocycles are expected to be versatile structural units for drug discovery.

  合成了七元杂环 [1,2,5] 三氮杂平和 [1,2,5] 氧杂二氮平衍生物，作为药物发现中替代传统哌嗪或吗啉的候选结构，提供了多个功能团修饰位点。我们首先合成了N保护的杂环，然后通过合成抗菌药物氟氯西林的类似物来验证其有效性。这些类似物表现出强大的体外和体内抗菌活性。特别是化合物10a在小鼠模型中采用静脉注射时，对抗耐甲氧西林金黄色葡萄球菌SR3637表现出良好的体内疗效。这些七元杂环有望成为药物发现中多功能的结构单元。