1-(6-p-tolyl-pyridin-3-yl)-ethanone | 1216790-93-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-(6-p-tolyl-pyridin-3-yl)-ethanone
• 英文别名: 1-[6-(4-Methylphenyl)pyridin-3-yl]ethanone
• CAS: 1216790-93-0
• 化学式: C₁₄H₁₃NO
• 分子量: 211.263
• InChiKey: XKKPZONXQYGSIZ-UHFFFAOYSA-N

物化性质

• 熔点：
  79-81 °C
• 沸点：
  357.2±27.0 °C(Predicted)
• 密度：
  1.079±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(6-p-tolyl-pyridin-3-yl)-ethanone 在 mercury(II) diacetate 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.08h， 生成
  参考文献：
  名称：

  Propargyl-Linked Antifolates are Dual Inhibitors of Candida albicans and Candida glabrata

  摘要：

  Species of Candida, primarily C. albicans and with increasing prevalence, C. glabrata, are responsible for the majority of fungal bloodstream infections that cause morbidity, especially among immune compromised patients. While the development of new antifungal agents that target the essential enzyme, dihydrofolate reductase (DHFR), in both Candida species would be ideal, previous attempts have resulted in antifolates that exhibit inconsistencies between enzyme inhibition and antifungal properties. In this article, we describe the evaluation of pairs of propargyl-linked antifolates that possess similar physicochemical properties but different shapes. All of these compounds are effective at inhibiting the fungal enzymes and the growth of C. glabrata; however, the inhibition of the growth of C. albicans is shape-dependent with extended para-linked compounds proving more effective than compact, meta-linked compounds. Using crystal structures of DHFR from C. albicans and C. glabrata bound to lead compounds, 13 new para-linked compounds designed to inhibit both species were synthesized. Eight of these compounds potently inhibit the growth of both fungal species with three compounds displaying dual MIC values less than 1 mu g/mL. Analysis of the active compounds shows that shape and distribution of polar functionality is critical in achieving dual antifungal activity.

  DOI：

  10.1021/jm401916j
• 作为产物：
  描述：

  4-甲苯硼酸 、 5-乙酰基-2-溴吡啶 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium carbonate 作用下， 以 水 、 乙腈 为溶剂， 反应 14.0h， 以92%的产率得到1-(6-p-tolyl-pyridin-3-yl)-ethanone
  参考文献：
  名称：

  Heterocyclic and Cyclic Analogs of Propargyl-Linked Inhibitors of Dihydrofolate Reductase

  摘要：

  式I和式IA的化合物是二氢叶酸还原酶的抑制剂，适用于二氢叶酸还原酶抑制或更具体地说，治疗真菌感染、细菌感染或原虫感染的组合物和方法，特定情况下，治疗由C. albicans或C. glabrata引起的真菌感染：其中R、R1、R2、R3、R4、A、B、E、V、W、X、Y和Z如本文所定义。

  公开号：

  US20150225353A1

文献信息

• Direct C−H Arylation of Electron-Deficient Heterocycles with Arylboronic Acids
  作者：Ian B. Seiple、Shun Su、Rodrigo A. Rodriguez、Ryan Gianatassio、Yuta Fujiwara、Adam L. Sobel、Phil S. Baran

  DOI：10.1021/ja1066459

  日期：2010.9.29

  A direct arylation of a variety of electron-deficient heterocycles with arylboronic acids has been developed. This new reaction proceeds readily at room temperature using inexpensive reagents: catalytic silver(I) nitrate in the presence of persulfate co-oxidant. The scope with respect to heterocycle and boronic acid coupling partner is broad, and sensitive functional groups are tolerated. This method

  已经开发了多种缺电子杂环与芳基硼酸的直接芳基化。这种新反应在室温下很容易使用廉价试剂进行：在过硫酸盐助氧化剂存在下催化硝酸银（I）。杂环和硼酸偶联伙伴的范围很广，敏感的官能团是可以容忍的。这种方法允许快速访问传统方法更难以访问的各种芳基化杂环。
• Heterocyclic and Cyclic Analogs of Propargyl-Linked Inhibitors of Dihydrofolate Reductase
  申请人：Wright Dennis L.

  公开号：US20150225353A1

  公开（公告）日：2015-08-13

  Compounds of Formula I and Formula IA are inhibitors of dihydrofolate reductase and are suitable for use in compositions and methods for dihydrofolate reductase inhibition or, more specifically, treatment of a fungal infection, a bacterial infection or a protozoal infection, and, in specific embodiments, treatment of a fungal infection caused by C. albicans or C. glabrata : wherein R, R 1 , R 2 , R 3 , R 4 , A, B, E, V, W, X, Y and Z are as defined herein.

  式I和式IA的化合物是二氢叶酸还原酶的抑制剂，适用于二氢叶酸还原酶抑制或更具体地说，治疗真菌感染、细菌感染或原虫感染的组合物和方法，特定情况下，治疗由C. albicans或C. glabrata引起的真菌感染：其中R、R1、R2、R3、R4、A、B、E、V、W、X、Y和Z如本文所定义。
• Heterocyclic and cyclic analogs of propargyl-linked inhibitors of dihydrofolate reductase
  申请人：Wright Dennis L

  公开号：US09382213B2

  公开（公告）日：2016-07-05

  Compounds of Formula I and Formula IA are inhibitors of dihydrofolate reductase and are suitable for use in compositions and methods for dihydrofolate reductase inhibition or, more specifically, treatment of a fungal infection, a bacterial infection or a protozoal infection, and, in specific embodiments, treatment of a fungal infection caused by C. albicans or C. glabrata: wherein R, R1, R2, R3, R4, A, B, E, V, W, X, Y and Z are as defined herein.

  式I和式IA的化合物是二氢叶酸还原酶的抑制剂，适用于用于二氢叶酸还原酶抑制的组合物和方法，更具体地说，用于治疗真菌感染、细菌感染或原虫感染，特别是用于治疗由C. albicans或C. glabrata引起的真菌感染的组合物和方法，其中R、R1、R2、R3、R4、A、B、E、V、W、X、Y和Z的定义如本文所述。
• Investigating the Catalytic Efficiency of Supported NHC‐Ag(I) Complexes in the Borono‐Minisci Reaction
  作者：Giada Moroni、Elena Bombonato、Samuele Bonafè、Alessandro Di Michele、Sara Presenti、Sara Guariento、Massimo Marcaccio、Roccaldo Sardella、Paolo Ronchi、Antimo Gioiello

  DOI：10.1002/cctc.202301654

  日期：——

  this paper we report the preparation, characterization, and evaluation of N-heterocyclic carbenes (NHC)-Ag(I) complexes as catalysts for the borono-Minisci reaction, a powerful and practical approach for the decoration of N-heterocycles. While it represents an unprecedented method, kinetic and cyclic voltammetric analyses evidenced how the complex structure influence the Ag(I)/Ag(II) redox potential

  在本文中，我们报道了 N-杂环卡宾 (NHC)-Ag(I) 配合物作为硼基​​-Minisci 反应催化剂的制备、表征和评估，这是一种强大且实用的 N-杂环装饰方法。虽然它代表了一种前所未有的方法，但动力学和循环伏安分析证明了复杂结构如何影响 Ag(I)/Ag(II) 氧化还原电位，进而影响反应效率和范围。
• US9382213B2
  申请人：——

  公开号：US9382213B2

  公开（公告）日：2016-07-05