methyl 3-(naphthalen-2-yl)benzoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl 3-(naphthalen-2-yl)benzoate
• 英文别名: Methyl 3-naphthalen-2-ylbenzoate
• 化学式: C₁₈H₁₄O₂
• 分子量: 262.308
• InChiKey: BIATZSCMACQSKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 3-(naphthalen-2-yl)benzoate 在 lithium hydroxide monohydrate 、 水 作用下， 以 甲醇 为溶剂， 反应 15.0h， 以93%的产率得到3-萘-2-苯甲酸
  参考文献：
  名称：

  Design, synthesis and structure–activity relationship studies of novel sirtuin 2 (SIRT2) inhibitors with a benzamide skeleton

  摘要：

  Human sirtuin 2 (SIRT2) is an attractive target molecule for development of drugs to treat neurodegenerative diseases and cancer, because SIRT2 inhibitors have a protective effect against neurodegeneration and an anti-proliferative effect on cancer stem cells. We designed and synthesized a series of benzamide derivatives as SIRT2 inhibitor candidates. Among them, compound 17k showed the most potent SIRT2-inhibitory activity (IC50 = 0.60 mu M), with more than 150-fold selectivity over SIRT1 and SIRT3 isoforms (IC50 > 100 mu M). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.11.027
• 作为产物：
  描述：

  3-溴苯甲酸甲酯 、 2-萘硼酸 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 3.5h， 以76%的产率得到methyl 3-(naphthalen-2-yl)benzoate
  参考文献：
  名称：

  Design, synthesis and structure–activity relationship studies of novel sirtuin 2 (SIRT2) inhibitors with a benzamide skeleton

  摘要：

  Human sirtuin 2 (SIRT2) is an attractive target molecule for development of drugs to treat neurodegenerative diseases and cancer, because SIRT2 inhibitors have a protective effect against neurodegeneration and an anti-proliferative effect on cancer stem cells. We designed and synthesized a series of benzamide derivatives as SIRT2 inhibitor candidates. Among them, compound 17k showed the most potent SIRT2-inhibitory activity (IC50 = 0.60 mu M), with more than 150-fold selectivity over SIRT1 and SIRT3 isoforms (IC50 > 100 mu M). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.11.027

文献信息

• Non-innocent electrophiles unlock exogenous base-free coupling reactions
  作者：Georgios Toupalas、Bill Morandi

  DOI：10.1038/s41929-022-00770-x

  日期：——

  metal-catalysed reactions rely on stoichiometric quantities of an exogenous base to enable catalytic turnover. Despite playing a fundamental role, the base poses major challenges, such as restricting the accessible chemical space or causing heterogeneous reaction mixtures. Here we introduce a unifying strategy that eliminates the need for an exogenous base through the use of non-innocent electrophiles (NIE)

  许多重要的过渡金属催化反应依赖于化学计量数量的外源碱来实现催化周转。尽管发挥了基础性作用，但碱基也带来了重大挑战，例如限制可接近的化学空间或导致多相反应混合物。在这里，我们介绍了一种统一策略，该策略通过使用非无辜亲电试剂 (NIE) 消除了对外源碱基的需求，NIE 配备了在反应过程中以受控方式释放的掩蔽碱基。通过将多个传统上依赖碱基的催化反应转变为外源无碱基均相过程，证明了这一概念的普遍适用性。此外，NIE 的优势特性在多个应用中得到了证明，例如在基于微摩尔级荧光的测定中。这导致发现了使用异丙醇作为良性还原剂的氨基甲酸芳基酯的镍催化脱氧反应。在更广泛的背景下，这项工作为 NIE 在催化中的战略利用提供了概念蓝图。
• [EN] GUANIDINE DERIVATIVES AS INHIBITORS OF Na/H EXCHANGE IN CELLS<br/>[FR] DERIVES DE GUANIDINE, UTILISES COMME INHIBITEURS DE L'ECHANGE DE Na/H DANS LES CELLULES
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：WO1994026709A1

  公开（公告）日：1994-11-24

  (EN) Guanidine derivatives of formula (I), wherein Y is N or C-R1 (in which R1 is hydrogen, lower alkyl, hydroxy, protected hydroxy, etc.), R2 is hydrogen, aryl which may have one suitable substituent, aryloxy, etc., R3 is hydrogen, lower alkoxy, hydroxy, protected hydroxy, etc., Z is N or C-R4 (in which R4 is hydrogen, carboxy, protected carboxy, nitro, halogen, hydroxy(lower)alkyl, etc.), and W is N or C-R12 (in which R12 is hydrogen, lower alkoxy, nitro, hydroxy or protected hydroxy), and pharmaceutically acceptable salts thereof which are useful as a medicament.(FR) L'invention se rapporte à des dérivés de guanidine, représentés par la formule (I), où Y représente N ou C-R1 (où R1 représente hydrogène, alkyle inférieur, hydroxy, hydroxy protégé, etc.), R2 représente hydrogène, aryle qui peut comporter un substituant approprié, aryloxy, etc., R3 représente hydrogène, alcoxy inférieur, hydroxy, hydroxy protégé, etc., Z représente N ou C-R4 (où R4 représente hydrogène, carboxy, carboxy protégé, nitro, halogène, hydroxy alkyle (inférieur), etc.), et W représente N ou C-R12 (où R12 représente hydrogène, alcoxy inférieur, nitro, hydroxy ou hydroxy protégé), ainsi qu'à des sels pharmaceutiquement acceptables de ces dérivés, utiles comme médicaments.

  (中) 公式(I)中的guanidine衍生物，其中Y是N或C-R1（其中R1是氢，低烷基，羟基，保护羟基等），R2是氢，芳基（可能有一个适当的取代基），芳氧基等，R3是氢，低烷氧基，羟基，保护羟基等，Z是N或C-R4（其中R4是氢，羧基，保护羧基，硝基，卤素，羟基（低）烷基等），W是N或C-R12（其中R12是氢，低烷氧基，硝基，羟基或保护羟基），以及其药学上可接受的盐，可用作药物。
• GUANIDINE DERIVATIVES AS INHIBITORS OF Na+ /H+ EXCHANGE IN CELLS
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP0699185A1

  公开（公告）日：1996-03-06
• US5824691A
  申请人：——

  公开号：US5824691A

  公开（公告）日：1998-10-20
• Design, synthesis and structure–activity relationship studies of novel sirtuin 2 (SIRT2) inhibitors with a benzamide skeleton
  作者：Taki Sakai、Yotaro Matsumoto、Minoru Ishikawa、Kazuyuki Sugita、Yuichi Hashimoto、Nobuhiko Wakai、Akio Kitao、Era Morishita、Chikashi Toyoshima、Tomoatsu Hayashi、Tetsu Akiyama

  DOI：10.1016/j.bmc.2014.11.027

  日期：2015.1

  Human sirtuin 2 (SIRT2) is an attractive target molecule for development of drugs to treat neurodegenerative diseases and cancer, because SIRT2 inhibitors have a protective effect against neurodegeneration and an anti-proliferative effect on cancer stem cells. We designed and synthesized a series of benzamide derivatives as SIRT2 inhibitor candidates. Among them, compound 17k showed the most potent SIRT2-inhibitory activity (IC50 = 0.60 mu M), with more than 150-fold selectivity over SIRT1 and SIRT3 isoforms (IC50 > 100 mu M). (C) 2014 Elsevier Ltd. All rights reserved.