1-烯丙基吡唑-4-甲醛 | 78758-36-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-烯丙基吡唑-4-甲醛
• 中文别名: 1-烯丙基-1H-吡唑-4-甲醛
• 英文名称: 1-allyl-1H-pyrazole-4-carbaldehyde
• 英文别名: 1-prop-2-enylpyrazole-4-carbaldehyde
• CAS: 78758-36-8
• 化学式: C₇H₈N₂O
• mdl: MFCD12827481
• 分子量: 136.153
• InChiKey: LIMBCPYABYDBSX-UHFFFAOYSA-N

物化性质

• 沸点：
  244.0±23.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933199090

反应信息

• 作为反应物：
  描述：

  1-烯丙基吡唑-4-甲醛 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 1.5h， 生成 4-(1-allyl-1H-pyrazol-4-yl)-2-amino-7,7-dimethyl-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile
  参考文献：
  名称：

  Synthesis of heterocyclic compounds from 4-formylpyrazoles

  摘要：

  吡唑和2,5-二甲基吡唑的甲酰化反应生成了多种含吡唑的醛，这些醛可用于合成克罗美烯、四氢克罗美烯、1,4-二氢吡喃[2,3-c]吡唑、吡喃[3,2-c]克罗美烯、硫克罗美烯[4,3-b]吡喃、吡喃[3,2-c]喹啉和噻唑[3,2-a]吡啶。

  DOI：

  10.1007/s11172-014-0451-8
• 作为产物：
  描述：

  N,N-二甲基甲酰胺 、 1-烯丙基-1H-吡唑 在 三氯氧磷 作用下， 反应 19.0h， 生成 1-烯丙基吡唑-4-甲醛
  参考文献：
  名称：

  Synthesis of heterocyclic compounds from 4-formylpyrazoles

  摘要：

  吡唑和2,5-二甲基吡唑的甲酰化反应生成了多种含吡唑的醛，这些醛可用于合成克罗美烯、四氢克罗美烯、1,4-二氢吡喃[2,3-c]吡唑、吡喃[3,2-c]克罗美烯、硫克罗美烯[4,3-b]吡喃、吡喃[3,2-c]喹啉和噻唑[3,2-a]吡啶。

  DOI：

  10.1007/s11172-014-0451-8

文献信息

• A Fine-Tuned Lipophilicity/Hydrophilicity Ratio Governs Antibacterial Potency and Selectivity of Bifurcated Halogen Bond-Forming NBTIs
  作者：Anja Kolarič、Maja Kokot、Martina Hrast、Matjaž Weiss、Irena Zdovc、Jurij Trontelj、Simon Žakelj、Marko Anderluh、Nikola Minovski

  DOI：10.3390/antibiotics10070862

  日期：——

  Herein, we report the design of a focused library of novel bacterial topoisomerase inhibitors (NBTIs) based on innovative mainly monocyclic right-hand side fragments active against DNA gyrase and Topo IV. They exhibit a very potent and wide range of antibacterial activity, even against some of the most concerning hard-to-treat pathogens for which new antibacterials are urgently needed, as reported by the WHO and CDC. NBTIs enzyme activity and whole cell potency seems to depend on the fine-tuned lipophilicity/hydrophilicity ratio that governs the permeability of those compounds through the bacterial membranes. Lipophilicity of NBTIs is apparently optimal for passing through the membrane of Gram-positive bacteria, but the higher, although not excessive lipophilicity and suitable hydrophilicity seems to determine the passage through Gram-negative bacterial membranes. However, due to the considerable hERG inhibition, which is still at least two orders of magnitude away from MICs, continued optimization is required to realize their full potential.

  在这里，我们报告了基于创新的主要单环右侧片段设计的新型细菌拓扑异构酶抑制剂（NBTIs）的库。这些片段对DNA旋转酶和Topo IV具有活性，表现出非常强大和广泛的抗菌活性，甚至对一些最令人担忧的难以治疗的病原体也有效，这些病原体迫切需要新的抗菌药物，正如世界卫生组织和疾病预防控制中心所报道的。NBTIs酶活性和整体细胞效力似乎取决于精细调节的亲脂性/亲水性比率，这个比率决定了这些化合物通过细菌膜的渗透性。NBTIs的亲脂性显然最适合通过革兰氏阳性细菌的膜，但更高的、尽管不过度的亲脂性和适当的亲水性似乎决定了通过革兰氏阴性细菌膜的通道。然而，由于对hERG的显著抑制，其至少比最小抑菌浓度高两个数量级，因此需要继续优化以发挥其全部潜力。
• Spiro-sulfonamide derivatives as inhibitors of myeloid cell leukemia-1 (MCL-1) protein
  申请人：Prelude Therapeutics Incorporated

  公开号：US11130769B2

  公开（公告）日：2021-09-28

  The disclosure is directed to compounds of Formula I Pharmaceutical compositions comprising compounds of Formula I as well as methods of their use and preparation, are also described.

  本公开涉及式 I 的化合物 还描述了包含式 I 化合物的药物组合物及其使用和制备方法。
• SPIRO-SULFONAMIDE DERIVATIVES AS INHIBITORS OF MYELOID CELL LEUKEMIA-1 (MCL-1) PROTEIN
  申请人：Prelude Therapeutics, Incorporated

  公开号：EP3877390A1

  公开（公告）日：2021-09-15
• Spiro-Sulfonamide Derivatives As Inhibitors Of Myeloid Cell Leukemia-1 (MCL-1) Protein
  申请人：Prelude Therapeutics Incorporated

  公开号：US20200148705A1

  公开（公告）日：2020-05-14

  The disclosure is directed to compounds of Formula I Pharmaceutical compositions comprising compounds of Formula I as well as methods of their use and preparation, are also described.
• Synthesis of heterocyclic compounds from 4-formylpyrazoles
  作者：V. Yu. Mortikov、L. A. Rodinovskaya、A. E. Fedorov、A. M. Shestopalov、P. A. Belyakov

  DOI：10.1007/s11172-014-0451-8

  日期：2014.2

  Formylation of pyrazole and 2,5-dimethylpyrazole gave a number of pyrazole-containing aldehydes, which can be used to obtain chromenes, tetrahydrochromenes, 1,4-dihydropyrano[2,3-c]pyrazoles, pyrano[3,2-c]chromenes, thiochromeno[4,3-b]pyrans, pyrano[3,2-c]-quinolines, and thiazolo[3,2-a]pyridines.

  吡唑和2,5-二甲基吡唑的甲酰化反应生成了多种含吡唑的醛，这些醛可用于合成克罗美烯、四氢克罗美烯、1,4-二氢吡喃[2,3-c]吡唑、吡喃[3,2-c]克罗美烯、硫克罗美烯[4,3-b]吡喃、吡喃[3,2-c]喹啉和噻唑[3,2-a]吡啶。