6,7,8,9-四氢-5H-苯并[7]环烯-2-羧酸 | 41068-24-0

• 分子结构分类: 有机化合物 - 苯类化合物
• 中文名称: 6,7,8,9-四氢-5H-苯并[7]环烯-2-羧酸
• 英文名称: 6,7,8,9-tetrahydro-5H-benzo[7]annulene-2-carboxylic acid
• 英文别名: 6,7,8,9-tetrahydro-5H-benzo[7]annulene-3-carboxylic acid
• CAS: 41068-24-0
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: WBFIRUDKSRDFDW-UHFFFAOYSA-N

物化性质

• 熔点：
  178 °C
• 沸点：
  346.7±31.0 °C(Predicted)
• 密度：
  1.142±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6,7,8,9-四氢-5H-苯并[7]环烯-2-羧酸 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以83%的产率得到(6,7,8,9-tetrahydro-5H-benzo[7]annulen-2-yl)methanol
  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 、 potassium hydroxide 作用下， 以 水 、 异丙醇 为溶剂， 反应 25.0h， 生成 6,7,8,9-四氢-5H-苯并[7]环烯-2-羧酸
  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

• [EN] MULTICYCLIC COMPOUNDS AND USE OF SAME FOR TREATING TUBERCULOSIS<br/>[FR] COMPOSÉS MULTICYCLIQUES ET LEUR UTILISATION POUR LE TRAITEMENT DE LA TUBERCULOSE
  申请人：HARVARD COLLEGE

  公开号：WO2019140254A1

  公开（公告）日：2019-07-18

  Provided herein are multicyclic compounds useful for treating tuberculosis. Also provided are methods of treating tuberculosis using the compounds of the invention.

  本文提供了用于治疗结核病的多环化合物。还提供了使用本发明化合物治疗结核病的方法。
• Benzoannulene derivatives as antiviral agents
  申请人：Southern Research Institute

  公开号：US11066357B2

  公开（公告）日：2021-07-20

  The present disclosure is concerned with benzoannulene compounds that are capable of inhibiting a viral infection and methods of treating viral infections such as, for example, chikungunya, Venezuelan equine encephalitis, dengue, influenza, and zika, using these compounds. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

  本公开涉及能够抑制病毒感染的苯并壬烯化合物，以及使用这些化合物治疗病毒感染的方法，例如基孔肯雅病毒、委内瑞拉马脑炎、登革热、流感和寨卡病毒。本摘要旨在作为在特定技术领域进行搜索的扫描工具，并非对本发明的限制。
• Vinblastine 20′ Amides: Synthetic Analogues That Maintain or Improve Potency and Simultaneously Overcome Pgp-Derived Efflux and Resistance
  作者：John C. Lukesh、Daniel W. Carney、Huijun Dong、R. Matthew Cross、Vyom Shukla、Katharine K. Duncan、Shouliang Yang、Daniel M. Brody、Manuela M. Brütsch、Aleksandar Radakovic、Dale L. Boger

  DOI：10.1021/acs.jmedchem.7b00958

  日期：2017.9.14

  A series of 180 vinblastine 20' amides were prepared in three steps from commercially available starting materials, systematically exploring a typically inaccessible site in the molecule enlisting a powerful functionalization strategy. Clear structure activity relationships and a structural model were developed in the studies which provided many such 20' amides that exhibit substantial and some even remarkable enhancements in potency, many that exhibit further improvements in activity against a Pgp overexpressing resistant cancer cell line, and an important subset of the vinblastine analogues that display little or no differential in activity against a matched pair of vinblastine sensitive and resistant (Pgp overexpressing) cell lines. The improvements in potency directly correlated with target tubulin binding affinity, and the reduction in differential functional activity against the sensitive and Pgp overexpressing resistant cell lines was found to correlate directly with an impact on Pgp-derived efflux.
• [EN] BENZOANNULENE DERIVATIVES AS ANTIVIRAL AGENTS<br/>[FR] DÉRIVÉS D'ANNULÈNE DE BENZÈNE EN TANT QU'AGENTS ANTIVIRAUX
  申请人：SOUTHERN RES INST

  公开号：WO2019133574A3

  公开（公告）日：2020-03-26
• Chloromethylation of ortho-disubstituted benzenes. A simple preparation of some useful .alpha. isomers of indan, tetralin, and benzosuberane
  作者：Robert H. Wightman、David E. Laycock

  DOI：10.1021/jo00405a018

  日期：1978.5