N-(2-methylphenyl)naphthalene-1-carboxamide | 302901-22-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(2-methylphenyl)naphthalene-1-carboxamide
• 英文别名: N-(o-tolyl)-1-naphthamide
• CAS: 302901-22-0
• 化学式: C₁₈H₁₅NO
• 分子量: 261.323
• InChiKey: VHKFOVJCOUMBFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(2-methylphenyl)naphthalene-1-carboxamide 、 benzhydryl triflate 在 sodium acetate 、 palladium diacetate 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以52%的产率得到6-(o-tolyl)benzo[i]phenanthridin-5(6H)-one
  参考文献：
  名称：

  钯催化芳基苯甲酰胺与二芳基碘鎓盐的环化

  摘要：

  通过使用二芳基碘鎓盐，在钯催化剂的存在下，通过邻位芳基化和C sp 2 -N 键形成的级联，在合成N-芳基菲啶酮衍生物中实现了环化。该反应表现出易于获得的N-芳基萘酰胺的广泛相容性。

  DOI：

  10.1002/adsc.202100860
• 作为产物：
  描述：

  1-萘甲酸 在 草酰氯 、 N,N-二异丙基乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 N-(2-methylphenyl)naphthalene-1-carboxamide
  参考文献：
  名称：

  N-苯基-1-萘酰胺的分子内脱氢光环化

  摘要：

  在这里，我们探索了一种N-取代萘甲酰胺的脱氢6π光环化方法，该方法可以在空气中进行。该方法采用DMSO作为反应溶剂和氧化剂，同时稳定底物的激发态。此外，光敏剂的添加使反应能够在 440-445 nm LED 光源下通过能量转移进行。所提出的机制最初通过 DFT 计算得到验证。

  DOI：

  10.1021/acs.orglett.4c01805

文献信息

• Preparation and Biological Properties of Ring-Substituted Naphthalene-1-Carboxanilides
  作者：Tomas Gonec、Jiri Kos、Eoghan Nevin、Rodney Govender、Matus Pesko、Jan Tengler、Ivan Kushkevych、Vendula Stastna、Michal Oravec、Peter Kollar、Jim O'Mahony、Katarina Kralova、Aidan Coffey、Josef Jampilek

  DOI：10.3390/molecules190710386

  日期：——

  In this study, a series of twenty-two ring-substituted naphthalene-1-carboxanilides were prepared and characterized. Primary in vitro screening of the synthesized carboxanilides was performed against Mycobacterium avium subsp. paratuberculosis. N-(2-Methoxyphenyl)naphthalene-1-carboxamide, N-(3-methoxy-phenyl)naphthalene-1-carboxamide, N-(3-methylphenyl)naphthalene-1-carboxamide, N-(4-methylphenyl)naphthalene-1-carboxamide and N-(3-fluorophenyl)naphthalene-1-carboxamide showed against M. avium subsp. paratuberculosis two-fold higher activity than rifampicin and three-fold higher activity than ciprofloxacin. The most effective antimycobacterial compounds demonstrated insignificant toxicity against the human monocytic leukemia THP-1 cell line. The testing of biological activity of the compounds was completed with the study of photosynthetic electron transport (PET) inhibition in isolated spinach (Spinacia oleracea L.) chloroplasts. The PET-inhibiting activity expressed by IC50 value of the most active compound N-[4-(trifluoromethyl)phenyl]naphthalene-1-carboxamide was 59 μmol/L. The structure-activity relationships are discussed.

  在这项研究中，合成了二十二种环取代的萘-1-羧酸酰胺，并进行了表征。对合成的羧酸酰胺进行了初步的体外筛选，以检测其对副结核分枝杆菌（Mycobacterium avium subsp. paratuberculosis）的活性。N-(2-甲氧基苯基)萘-1-羧酸酰胺、N-(3-甲氧基苯基)萘-1-羧酸酰胺、N-(3-甲基苯基)萘-1-羧酸酰胺、N-(4-甲基苯基)萘-1-羧酸酰胺和N-(3-氟苯基)萘-1-羧酸酰胺对副结核分枝杆菌的活性是利福平的两倍，且是环丙沙星的三倍。最有效的抗分枝杆菌化合物对人单核细胞白血病THP-1细胞株表现出微不足道的毒性。通过研究分离的菠菜（Spinacia oleracea L.）叶绿体中的光合电子传递（PET）抑制来完成对化合物生物活性的测试。最活跃的化合物N-[4-(三氟甲基)苯基]萘-1-羧酸酰胺的PET抑制活性以IC50值表示为59 μmol/L。讨论了结构-活性关系。
• BCL-3 INHIBITORS
  申请人：University College Cardiff Consultants Limited

  公开号：EP3628374A2

  公开（公告）日：2020-04-01

  The present application relates to compounds of any one of Formulae I, Ia, Ib, Ic, Id, Ie, and If. Compounds of Formula I have the structure: wherein A, B, Y, Z, R2, R4, R5, R6, Rq and q are as defined herein. The compounds can be used as inhibitors of Bcl-3 and can be used for the treatment of cancer, particularly metastatic cancer.

  本申请涉及式 I、Ia、Ib、Ic、Id、Ie 和 If 中任何一种的化合物。式 I 的化合物具有如下结构 其中 A、B、Y、Z、R2、R4、R5、R6、Rq 和 q 如本文所定义。这些化合物可用作 Bcl-3 的抑制剂，并可用于治疗癌症，特别是转移性癌症。
• Highly Efficient Aminocarbonylation of Iodoarenes at Atmospheric Pressure Catalyzed by a Robust Acenaphthoimidazolyidene Allylic Palladium Complex
  作者：Weiwei Fang、Qinyue Deng、Mizhi Xu、Tao Tu

  DOI：10.1021/ol401550h

  日期：2013.7.19

  A robust allylic palladium-NHC complex was developed and exhibited extremely high catalytic activity toward aminocarbonylation of various (hetero)aryl iodides under atmospheric carbon monoxide pressure, in which a broad range of secondary and primary amines were well tolerated. In addition, the concise synthesis of an anticancer drug tamibarotene was accomplished even in a gram scale, further highlighting the practical applicability of the protocol.
• PIGMENT COMPOSITIONS, COLORED COMPOSITIONS MAKING USE OF THE PIGMENT COMPOSITIONS, AND COLOR FILTERS
  申请人：HOSHINO Ryo

  公开号：US20080107977A1

  公开（公告）日：2008-05-08

  Pigment compositions each contain an organic pigment and at least one compound selected from compounds represented by the following formulas (I) or (II), respectively: A-N═N-D, B—N═N-D or C—N═N-D   Formula (I) A-N═N—CH(COCH 3 )—CONH-E, B—N═N—CH(COCH 3 )—CONH-E or C—N═N—CH(COCH 3 )—CONH-E   Formula (II) wherein A represents a substituted or unsubstituted phenyl group, B represents a substituted or unsubstituted β-naphthyl group, C represents a substituted or unsubstituted α-anthraquinonyl group, D represents a particular substituted aromatic group, and E represents a substituted or unsubstituted phenyl group, with a proviso that the compounds each have at least one substituent represented by —COOM or —SO 3 M in which M represents a hydrogen atom, metal atom, ammonium group, organic amine group or quaternary ammonium group. Colored compositions making use of the pigment compositions and color filters making use of the colored compositions are also disclosed.
• Pigment compositions, colored compositions making use of the pigment compositions, and color filters
  申请人：Hoshino Ryo

  公开号：US20100065794A1

  公开（公告）日：2010-03-18

  Pigment compositions each contain an organic pigment and at least one compound selected from compounds represented by the following formula (II), respectively: A-N═N—CH(COCH 3 )—CONH-E, B—N═N—CH(COCH 3 )—CONH-E or C—N═N—CH(COCH 3 )—CONH-E, wherein A represents a substituted or unsubstituted phenyl group, B represents a substituted or unsubstituted β-naphthyl group, C represents a substituted or unsubstituted α-anthraquinonyl group, D represents a particular substituted aromatic group, and E represents a substituted or unsubstituted phenyl group, with a proviso that the compounds each have at least one substituent represented by —COOM or —SO 3 M in which M represents a hydrogen atom, metal atom, ammonium group, organic amine group or quaternary ammonium group. Colored compositions making use of the pigment compositions and color filters making use of the colored compositions are also disclosed.