4-(3-氯苯甲酰基)吡啶 | 62246-94-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-(3-氯苯甲酰基)吡啶
• 中文别名: (3-氯苯基)-吡啶-4-基-甲酮
• 英文名称: (3-chlorophenyl)(pyridin-4-yl)methanone
• 英文别名: 3-Chlorphenyl-4-pyridyl-keton；(3-chlorophenyl)-pyridin-4-ylmethanone
• CAS: 62246-94-0
• 化学式: C₁₂H₈ClNO
• mdl: MFCD08696076
• 分子量: 217.655
• InChiKey: JPQDGWGFDQVTFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  4-(3-氯苯甲酰基)吡啶 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以79%的产率得到4-(3-chlorobenzoyl)pyridine 1-oxide
  参考文献：
  名称：

  靶向 CCR9 细胞内结合位点的化学生物学工具箱：荧光配体、新药先导物和 PROTAC

  摘要：

  基于细胞内 CCR9 拮抗剂 vercirnon，我们开发了第一个基于小分子的荧光配体，靶向 GPCR 的细胞内变构结合位点 (IABS)。该工具能够通过 NanoBRET、荧光显微镜进行结合研究，并发现具有更高亲和力的新型细胞内 CCR9 拮抗剂。为了诱导 CCR9 降解，我们开发了第一个针对 GPCR 的 IABS 的 PROTAC。

  DOI：

  10.1002/anie.202116782
• 作为产物：
  描述：

  4-氰基吡啶 在 三氯化硼 、 sodium hydrogensulfite 、 溶剂黄146 、 sodium nitrite 作用下， 以 乙醇 、 二氯甲烷 、 三氯乙烯 、 水 为溶剂， 反应 26.42h， 生成 4-(3-氯苯甲酰基)吡啶
  参考文献：
  名称：

  靶向 CCR9 细胞内结合位点的化学生物学工具箱：荧光配体、新药先导物和 PROTAC

  摘要：

  基于细胞内 CCR9 拮抗剂 vercirnon，我们开发了第一个基于小分子的荧光配体，靶向 GPCR 的细胞内变构结合位点 (IABS)。该工具能够通过 NanoBRET、荧光显微镜进行结合研究，并发现具有更高亲和力的新型细胞内 CCR9 拮抗剂。为了诱导 CCR9 降解，我们开发了第一个针对 GPCR 的 IABS 的 PROTAC。

  DOI：

  10.1002/anie.202116782

文献信息

• Photocatalyst-controlled and visible light-enabled selective oxidation of pyridinium salts
  作者：Xiang-Jun Peng、Hai-Ping He、Qian Liu、Kun She、Bao-Qi Zhang、Heng-Shan Wang、Hai-Tao Tang、Ying-Ming Pan

  DOI：10.1007/s11426-020-9958-6

  日期：2021.5

  methods of photocatalytic-controlled and visible light-induced selective oxidation of pyridiniums with air as the terminal oxidant. The key to these transformations is to choose the appropriate light source and photocatalyst. Pyridiniums are successfully converted into pyrroles through oxygen-mediated cycloaddition, proton-coupled electron transfer (PCET), pyridine ring opening, and recyclization. The

  这项研究提出了两种不同的方法，以空气为末端氧化剂，可光催化控制和可见光诱导的吡啶鎓的选择性氧化。这些转变的关键是选择合适的光源和光催化剂。吡啶鎓通过氧介导的环加成，质子偶联电子转移（PCET），吡啶开环和再循环成功地转化为吡咯。另一途径是吡啶鎓在钴（II）的催化下通过自由基重排/好氧氧化选择性地形成4-羰基吡啶。
• A Multifunctional Reagent Designed for the Site-Selective Amination of Pyridines
  作者：Patrick S. Fier、Suhong Kim、Ryan D. Cohen

  DOI：10.1021/jacs.0c03537

  日期：2020.5.13

  We report the development of a multifunctional reagent for the direct conversion of pyridines to Boc-protected 2-aminopyridines with exquisite site selectivity and chemoselectivity. The novel reagent was prepared on 200-g scale in a single step, reacts in the title reaction under mild conditions without precautions toward air or moisture, and is tolerant of nearly all common functionality. Experimental and in situ spectroscopic monitoring techniques provide detailed insights and unexpected findings for the unique reaction mechanism.
• Clotrimazole Scaffold as an Innovative Pharmacophore Towards Potent Antimalarial Agents: Design, Synthesis, and Biological and Structure–Activity Relationship Studies
  作者：Sandra Gemma、Giuseppe Campiani、Stefania Butini、Gagan Kukreja、Salvatore Sanna Coccone、Bhupendra P. Joshi、Marco Persico、Vito Nacci、Isabella Fiorini、Ettore Novellino、Ernesto Fattorusso、Orazio Taglialatela-Scafati、Luisa Savini、Donatella Taramelli、Nicoletta Basilico、Silvia Parapini、Giulia Morace、Vanessa Yardley、Simon Croft、Massimiliano Coletta、Stefano Marini、Caterina Fattorusso

  DOI：10.1021/jm701247k

  日期：2008.3.13

  We describe herein the design, synthesis, biological evaluation, and structure-activity relationship (SAR) studies of an innovative class of antimalarial agents based on a polyaromatic pharmacophore structurally related to clotrimazole and easy to synthesize by low-cost synthetic procedures. SAR studies delineated a number of structural features able to modulate the in vitro and in vivo antimalarial activity. A selected set of antimalarials was further biologically investigated and displayed low in vitro toxicity on a panel of human and murine cell lines. In vitro, the novel compounds proved to be selective for free heme, as demonstrated in the beta-hematin inhibitory activity assay, and did not show inhibitory activity against 14-alpha-lanosterol demethylase (a fungal P450 cytochrome). Compounds 2, 4e, and 4n exhibited in vivo activity against P. chabaudi after oral administration and thus represent promising antimalarial agents for further preclinical development.
• WO2007/104696
  申请人：——

  公开号：——

  公开（公告）日：——
• Chlorpheniramine Analogues Reverse Chloroquine Resistance in <i>Plasmodium falciparum</i> by Inhibiting PfCRT
  作者：Karen J. Deane、Robert L. Summers、Adele M. Lehane、Rowena E. Martin、Russell A. Barrow

  DOI：10.1021/ml5000228

  日期：2014.5.8

  The emergence and spread of malaria parasites that are resistant to chloroquine (CQ) has been a disaster for world health. The antihistamine chlorpheniramine (CP) partially resensitizes CQ-resistant (CQR) parasites to CQ but possesses little intrinsic antiplasmodial activity. Mutations in the parasite's CQ resistance transporter (PfCRT) confer resistance to CQ by enabling the protein to transport the drug away from its site of action, and it is thought that resistance-reversers such as CP exert their effect by blocking this CQ transport activity. Here, a series of new structural analogues and homologues of CP have been synthesized. We show that these compounds (along with other in vitro CQ resistance-reversers) inhibit the transport of CQ via a resistance-conferring form of PfCRT expressed in Xenopus laevis oocytes. Furthermore, the level of PfCRT-inhibition was found to correlate well with both the restoration of CQ accumulation and the level of CQ resensitization in CQR parasites.