(6,7,8,9-tetrahydro-5H-benzo[7]annulen-2-yl)methanamine | 767629-81-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (6,7,8,9-tetrahydro-5H-benzo[7]annulen-2-yl)methanamine
• 英文别名: C-(6,7,8,9-tetrahydro-5H-benzocycloheptene-2-yl)methylamine；6,7,8,9-tetrahydro-5H-benzo[7]annulen-3-ylmethanamine
• CAS: 767629-81-2
• 化学式: C₁₂H₁₇N
• 分子量: 175.274
• InChiKey: RCMAVVJYORHURE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  (6,7,8,9-tetrahydro-5H-benzo[7]annulen-2-yl)methanamine 在 盐酸 、 sodium tetrahydroborate 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 17.02h， 生成 (E)-3-phenyl-N-((6,7,8,9-tetrahydro-5H-benzo[7]annulen-2-yl)-methyl)prop-2-en-1-amine hydrochloride
  参考文献：
  名称：

  Discovery of Benzocycloalkane Derivatives Efficiently Blocking Bacterial Virulence for the Treatment of Methicillin-Resistant S. aureus (MRSA) Infections by Targeting Diapophytoene Desaturase (CrtN)

  摘要：

  Antivirulence strategies are now attracting interest for the inherent mechanism of action advantages. In our previous work, diapophytoene desaturase (CrtN) was identified to be an attractive and drugable target for fighting pigmented S. aureus infections. In this research, we developed a series of effective benzocycloalkane-derived CrtN inhibitors with submicromolar IC50. Analogue 8 blocked the pigment biosynthesis of three MRSA strains with a nanomolar IC50 value. Corresponding to its mode of action, 8 did not function as a bactericidal agent. 8 could sensitize S. aureus to immune clearance. In vivo, 8 was proven to be efficacious in an S. aureus Newman sepsis model and abscess formation model. For two typical MRSAs,. USA400 MW2 and Mu50, 8 significantly decreased the staphylococcal loads in the liver and kidneys. Moreover, 8 showed minimal antifungal activity compared to that of NTF. In summary, 8 has the potential to be developed as a therapeutic drug, especially against intractable MRSA issues.

  DOI：

  10.1021/acs.jmedchem.6b00122
• 作为产物：
  描述：

  1-苯并环庚酮 在 三乙基硅烷 、 N-碘代丁二酰亚胺 、 溶剂黄146 、 三氟乙酸 作用下， 反应 11.0h， 生成 (6,7,8,9-tetrahydro-5H-benzo[7]annulen-2-yl)methanamine
  参考文献：
  名称：

  Discovery of Benzocycloalkane Derivatives Efficiently Blocking Bacterial Virulence for the Treatment of Methicillin-Resistant S. aureus (MRSA) Infections by Targeting Diapophytoene Desaturase (CrtN)

  摘要：

  Antivirulence strategies are now attracting interest for the inherent mechanism of action advantages. In our previous work, diapophytoene desaturase (CrtN) was identified to be an attractive and drugable target for fighting pigmented S. aureus infections. In this research, we developed a series of effective benzocycloalkane-derived CrtN inhibitors with submicromolar IC50. Analogue 8 blocked the pigment biosynthesis of three MRSA strains with a nanomolar IC50 value. Corresponding to its mode of action, 8 did not function as a bactericidal agent. 8 could sensitize S. aureus to immune clearance. In vivo, 8 was proven to be efficacious in an S. aureus Newman sepsis model and abscess formation model. For two typical MRSAs,. USA400 MW2 and Mu50, 8 significantly decreased the staphylococcal loads in the liver and kidneys. Moreover, 8 showed minimal antifungal activity compared to that of NTF. In summary, 8 has the potential to be developed as a therapeutic drug, especially against intractable MRSA issues.

  DOI：

  10.1021/acs.jmedchem.6b00122

文献信息

• Amide compound and method of controlling plant disease with the same
  申请人：Sakaguchi Hiroshi

  公开号：US20060122065A1

  公开（公告）日：2006-06-08

  A amid compound of the formula (1): wherein, in the formula, R 51 represents a halogen atom, a C1-C6 alkyl group and the like; R 52 represents a hydrogen atom, a halogen atom, a C1-C6 alkyl group and the like; R 53 represents a halogen atom and the like; R 56 represents a halogen atom and the like; R 57 represents a hydrogen atom and the like; R 58 and R 59 independently represent a hydrogen atom, a C1-C3 alkyl group and the like; R 60 represents a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C3-C4 alkenyl group, or a C3-C6 alkynyl group; R 61 represents a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C3-C4 alkenyl group or a C3-C6 alkynyl group or a C2-C4 cyanoalkyl group; R 62 , R 63 and R 64 represent a hydrogen atom, a halogen atom and the like; X represents a oxygen atom or a sulfur atom; has an excellent activity against plant diseases.

  一种化合物的公式（1）：其中，在公式中，R51代表卤素原子，C1-C6烷基等；R52代表氢原子，卤素原子，C1-C6烷基等；R53代表卤素原子等；R56代表卤素原子等；R57代表氢原子等；R58和R59分别独立地代表氢原子，C1-C3烷基等；R60代表C1-C4烷基，C1-C4卤代烷基，C3-C4烯基或C3-C6炔基；R61代表C1-C4烷基，C1-C4卤代烷基，C3-C4烯基或C3-C6炔基或C2-C4氰基烷基；R62，R63和R64代表氢原子，卤素原子等；X代表氧原子或硫原子；具有出色的植物病害活性。
• AMIDE COMPOUND AND METHOD OF CONTROLLING PLANT DISEASE WITH THE SAME
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP1577290A1

  公开（公告）日：2005-09-21

  A amid compound of the formula (1): wherein, in the formula, R51 represents a halogen atom, a C1-C6 alkyl group and the like; R52 represents a hydrogen atom, a halogen atom, a C1-C6 alkyl group and the like; R53 represents a halogen atom and the like; R56 represents a halogen atom and the like; R57 represents a hydrogen atom and the like; R58 and R59 independently represent a hydrogen atom, a C1-C3 alkyl group and the like; R60 represents a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C3-C4 alkenyl group, or a C3-C6 alkynyl group; R61 represents a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C3-C4 alkenyl group or a C3-C6 alkynyl group or a C2-C4 cyanoalkyl group; R62, R63 and R64 represent a hydrogen atom, a halogen atom and the like; X represents a oxygen atom or a sulfur atom; has an excellent activity against plant diseases.

  一种式（1）的酰胺化合物： 式中 R51 代表卤素原子、C1-C6 烷基等； R52 代表氢原子、卤素原子、C1-C6 烷基等； R53 代表卤素原子等； R56 代表卤原子等； R57 代表氢原子等； R58 和 R59 独立地代表氢原子、C1-C3 烷基等； R60 代表 C1-C4 烷基、C1-C4 卤代烷基、C3-C4 烯基或 C3-C6 烷炔基；R61代表 C1-C4 烷基、C1-C4 卤代烷基、C3-C4 烯基或 C3-C6 炔基或 C2-C4 氰烷基；R62、R63 和 R64 代表氢原子、卤素原子等；X 代表氧原子或硫原子； 对植物病害具有极佳的活性。
• [EN] 6,7,8,9-四氢-5H-苯并[7]轮烯-2-烷基胺类化合物及其用途 6,7,8,9-TETRAHYDRO-5H-BENZO[7] ANNULENE-2-ALKYLAMINE COMPOUND AND USE THEREOF<br/>[FR] COMPOSÉ DE 6,7,8,9-TÉTRAHYDRO-5H-BENZO[7]ANNULÈNE-2-ALKYLAMINE ET SON UTILISATION<br/>[ZH] 6,7,8,9-四氢-5H-苯并[7]轮烯-2-烷基胺类化合物及其用途
  申请人：UNIV EAST CHINA SCIENCE & TECH

  公开号：WO2015188309A1

  公开（公告）日：2015-12-17

  本发明提供了式I所示的6，7，8，9-四氢-5H-苯并[7]轮烯-2-烷基胺类化合物或其在药学上可接受的盐及其用途。该类化合物对金黄色葡萄球菌的金黄色色素的合成显示出较强的抑制活性。金黄色葡萄球菌的金黄色色素具有帮助金黄色葡萄球菌逃避人体先天免疫系统产生的活性氧的杀害的能力，是决定细菌致病能力的一个关键毒力因子。金黄色色素还可以增加细菌对油酸的抵抗能力，通过提高细菌抗氧化的能力从而增加细菌的毒力。抑制金黄色葡萄球菌的毒力因子金黄色色素合成是新的、有效的抗菌药物策略。本发明的化合物通过靶向抑制金黄色色素的合成，不但有望开发成新型的单一用药方式的抗菌药物，而且还可以开发成与现有抗生素组合给药方式的抗菌药物。