2-((4-(4-trifluoromethylbenzyl)piperazin-1-yl)methyl)-3-hydroxy-6-(chloromethyl)-4H-pyran-4-one | 1428245-50-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-((4-(4-trifluoromethylbenzyl)piperazin-1-yl)methyl)-3-hydroxy-6-(chloromethyl)-4H-pyran-4-one
• 英文别名: 6-(Chloromethyl)-3-hydroxy-2-[[4-[[4-(trifluoromethyl)phenyl]methyl]piperazin-1-yl]methyl]pyran-4-one；6-(chloromethyl)-3-hydroxy-2-[[4-[[4-(trifluoromethyl)phenyl]methyl]piperazin-1-yl]methyl]pyran-4-one
• CAS: 1428245-50-4
• 化学式: C₁₉H₂₀ClF₃N₂O₃
• 分子量: 416.828
• InChiKey: CNZSFXIZNFEZQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  53
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  曲酸 在 氯化亚砜 作用下， 以 甲醇 为溶剂， 生成 2-((4-(4-trifluoromethylbenzyl)piperazin-1-yl)methyl)-3-hydroxy-6-(chloromethyl)-4H-pyran-4-one
  参考文献：
  名称：

  Evaluation of bioactivities of chlorokojic acid derivatives against dermatophytes couplet with cytotoxicity

  摘要：

  In an attempt to find novel antifungal agents with improved activity, a series of compounds bearing 6-chloromethyl-3-hydroxy-2-substituted 4H-pyran-4-one moiety were synthesized and examined for their cytotoxic evaluation and antifungal activities against both standard and isolated dermatophytic fungal species Microsporum gypseum, Trichophyton mentagrophytes var. erinacei and Epidermophyton floccosum. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.098

文献信息

• Evaluation of bioactivities of chlorokojic acid derivatives against dermatophytes couplet with cytotoxicity
  作者：Mutlu Dilsiz Aytemir、Berrin Özçelik、Gülşah Karakaya

  DOI：10.1016/j.bmcl.2013.03.098

  日期：2013.6

  In an attempt to find novel antifungal agents with improved activity, a series of compounds bearing 6-chloromethyl-3-hydroxy-2-substituted 4H-pyran-4-one moiety were synthesized and examined for their cytotoxic evaluation and antifungal activities against both standard and isolated dermatophytic fungal species Microsporum gypseum, Trichophyton mentagrophytes var. erinacei and Epidermophyton floccosum. (C) 2013 Elsevier Ltd. All rights reserved.
• [EN] ANTI CANCER AND ANTI TYROSINASE ACTIVITIES OF KOJIC ACID DERIVED COMPOUNDS<br/>[FR] ACTIVITÉS ANTICANCÉREUSES ET ANTI-TYROSINASE DE COMPOSÉS DÉRIVÉS DE L'ACIDE KOJIQUE
  申请人：AYTEMIR MUTLU

  公开号：WO2019194769A2

  公开（公告）日：2019-10-10

  The invention is related to compounds within the structure of kojic acid derived Mannich bases, hydrates, solvates, pharmacologically acceptable salts and geometric isomers thereof which show high inhibition against fungal tyrosinases (T3824) while expressing cytotoxic features against the A375 (ATCC CRL-1619) human malignant cell line, and at the same time which do not express cytotoxicity against HGF-1 and MRC-5 human fibroblast cell lines, and aside from this which suppresses melanogenesis in A375 cells that are aimed to be used in melanoma treatment due to all of these effects.
• Design, synthesis and <i>in vivo</i>/<i>in vitro</i> screening of novel chlorokojic acid derivatives
  作者：Gülşah Karakaya、Mutlu Dilsiz Aytemir、Berrin Özçelik、Ünsal Çalış

  DOI：10.3109/14756366.2012.666538

  日期：2013.6.1

  A series of novel Mannich bases of chlorokojic acid (2-chloromethyl-5-hydroxy-4H-pyran-4-one) were synthesized and their biological activities were investigated. Anticonvulsant activity results according to phase-I tests of Antiepileptic Drug Development (ADD) Program revealed that compound 13 was the most effective one at 4 h against subcutaneous pentylenetetrazole (scPTZ)-induced seizure test. Antimicrobial activities were evaluated in vitro against bacteria and fungi by using broth microdilution method. The antitubercular activities against Mycobacterium tuberculosis and M. avium were discussed with Resazurin microplate assay (REMA). The antimicrobial activity results indicated that compounds 1 and 12 (MIC: 8-16 mu g/mL) showed higher activity against Gram negative bacteria while compound 12 had MIC: 4-16 mu g/mL against Gram positive bacteria. Compound 1 was the most active one with MIC values of 8-32 mu g/mL against fungi. Mannich bases also exhibit significant antitubercular activity in a MIC range of 4 to 32 mu g/mL, especially compound 18 against M. avium.