N-[[1(benzyloxycarbonyl)-piperidin-3-yl]-oxy]-phthalimide | 171906-17-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-[[1(benzyloxycarbonyl)-piperidin-3-yl]-oxy]-phthalimide
• 英文别名: benzyl 3-(1,3-dioxoisoindol-2-yl)oxypiperidine-1-carboxylate
• CAS: 171906-17-5
• 化学式: C₂₁H₂₀N₂O₅
• 分子量: 380.4
• InChiKey: RLNDDSAHECHMFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  76.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[[1(benzyloxycarbonyl)-piperidin-3-yl]-oxy]-phthalimide 在 水 、 肼 作用下， 以 乙醇 为溶剂， 生成 3-Aminooxy-piperidine-1-carboxylic acid benzyl ester
  参考文献：
  名称：

  Method of treating tuberculosis

  摘要：

  揭示了用于治疗结核病的大环内酯类和酮内酯类药物，以及包含它们的组合物。还公开了使用大环内酯类和酮内酯类药物以及包含它们的组合物治疗结核病的方法。

  公开号：

  US20050014706A1
• 作为产物：
  描述：

  3-羟基哌啶 在 azodiethyl dicarboxylate 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 24.0h， 生成 N-[[1(benzyloxycarbonyl)-piperidin-3-yl]-oxy]-phthalimide
  参考文献：
  名称：

  Synthesis and Antibacterial Activity of Ketolides (6-O-Methyl-3-oxoerythromycin Derivatives):  A New Class of Antibacterials Highly Potent Against Macrolide-Resistant and -Susceptible Respiratory Pathogens

  摘要：

  In the search for new antibiotics active against macrolide-resistant pneumococci and Haemophilus influenzae, we synthesized a new class of 3-oxo-6-O-methylerythromycin derivatives, so-called "ketolides". A keto function was introduced in position 3 after removal of L-cladinose, a sugar which has long been thought essential. Further modifications of the macrolactone backbone allowed us to obtain three different series of 9-oxime, 11,12-carbamate, and 11,12-hydrazonocarbamate ketolides. These compounds were found to be very active against penicillin/erythromycin-resistant pneumococci and noninducers of MLS(B) resistance. The 11,12-substituted ketolide 61 (HMR 3004) demonstrated a potent activity against multiresistant pneumococci associated with a well-balanced activity against all bacteria involved in respiratory infections including H. influenzae, Mycoplasma catarrhalis, group A streptococci, and atypical bacteria. In addition HMR 3004 displayed high therapeutic activity in animals infected by all major strains, irrespective of their resistance phenotype.

  DOI：

  10.1021/jm980240d

文献信息

• Method of treating tuberculosis
  申请人：Falzari Kanakeshwari

  公开号：US20050014706A1

  公开（公告）日：2005-01-20

  Macrolide and ketolides, and compositions containing the same, useful in the treatment of tuberculosis are disclosed. Methods of treating tuberculosis using the macrolides and ketolides, and compositions containing the same, also are disclosed.

  揭示了用于治疗结核病的大环内酯类和酮内酯类药物，以及包含它们的组合物。还公开了使用大环内酯类和酮内酯类药物以及包含它们的组合物治疗结核病的方法。
• Erythromycin compounds
  申请人：Roussel UCLAF

  公开号：US05444051A1

  公开（公告）日：1995-08-22

  Compounds of the formula ##STR1## wherein X and X' form C.dbd.O or C.dbd.NOR, R is selected from the group consisting of hydrogen, heterocycle, alkyl, alkenyl, alkynyl, all optionally substituted, or X is ##STR2## R.sub.a and R.sub.b are hydrogen or a hydrocarbon group or form together with the nitrogen a heterocycle, or with A forms a 9-N, 11-O ring, and X' is hydrogen, --Y and Y' have the same definition as X and X', B is hydrogen or OR.sub.4, R.sub.4 is hydrogen or forms together with A a carbonate or a carbamate, A forms with C a double bond or A is OR'.sub.4, R'.sub.4 is hydrogen or forms together with B a carbonate or ##STR3## R.sub.2 is alkyl or --CONH.sub.2, --CONHCOR.sub.11 or --CONHSO.sub.2 R.sub.11, R.sub.11 is a hydrocarbon up to 18 carbon atoms, R.sub.3 is hydrogen, ##STR4## and Z is hydrogen or a carboxylic acid remainder and their non-toxic, pharmaceutically acceptable acid addition salts, their preparation and intermediates useful as antibiotics.

  式为##STR1##的化合物，其中X和X'形成C.dbd.O或C.dbd.NOR，R从氢、杂环、烷基、烯烃、炔烃组成的群体中选择，所有这些都可以选择性地被取代，或者X是##STR2##，R.sub.a和R.sub.b是氢或一个碳氢基团，或者与氮一起形成一个杂环，或者与A一起形成一个9-N、11-O环，X'是氢，--Y和Y'的定义与X和X'相同，B是氢或OR.sub.4，R.sub.4是氢或与A一起形成碳酸酯或氨基甲酸酯，A与C形成双键或A是OR'.sub.4，R'.sub.4是氢或与B一起形成碳酸酯或##STR3##，R.sub.2是烷基或--CONH.sub.2，--CONHCOR.sub.11或--CONHSO.sub.2 R.sub.11，R.sub.11是碳原子数多达18的碳氢基团，R.sub.3是氢，##STR4##，Z是氢或羧酸残基及其无毒、药学上可接受的酸盐，它们的制备和中间体可用作抗生素。
• US5444051A
  申请人：——

  公开号：US5444051A

  公开（公告）日：1995-08-22
• US5561118A
  申请人：——

  公开号：US5561118A

  公开（公告）日：1996-10-01
• Synthesis and Antibacterial Activity of Ketolides (6-<i>O</i>-Methyl-3-oxoerythromycin Derivatives):  A New Class of Antibacterials Highly Potent Against Macrolide-Resistant and -Susceptible Respiratory Pathogens
  作者：Constantin Agouridas、Alexis Denis、Jean-Michel Auger、Yannick Benedetti、Alain Bonnefoy、François Bretin、Jean-François Chantot、Arlette Dussarat、Claude Fromentin、Solange Gouin D'Ambrières、Sylvette Lachaud、Patrick Laurin、Odile Le Martret、Véronique Loyau、Nicole Tessot

  DOI：10.1021/jm980240d

  日期：1998.10.1

  In the search for new antibiotics active against macrolide-resistant pneumococci and Haemophilus influenzae, we synthesized a new class of 3-oxo-6-O-methylerythromycin derivatives, so-called "ketolides". A keto function was introduced in position 3 after removal of L-cladinose, a sugar which has long been thought essential. Further modifications of the macrolactone backbone allowed us to obtain three different series of 9-oxime, 11,12-carbamate, and 11,12-hydrazonocarbamate ketolides. These compounds were found to be very active against penicillin/erythromycin-resistant pneumococci and noninducers of MLS(B) resistance. The 11,12-substituted ketolide 61 (HMR 3004) demonstrated a potent activity against multiresistant pneumococci associated with a well-balanced activity against all bacteria involved in respiratory infections including H. influenzae, Mycoplasma catarrhalis, group A streptococci, and atypical bacteria. In addition HMR 3004 displayed high therapeutic activity in animals infected by all major strains, irrespective of their resistance phenotype.