4-isopropylcinnamoyl chloride | 846552-80-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 4-isopropylcinnamoyl chloride
• 英文别名: 3-(4-propan-2-ylphenyl)prop-2-enoyl chloride
• CAS: 846552-80-5
• 化学式: C₁₂H₁₃ClO
• mdl: MFCD11107996
• 分子量: 208.688
• InChiKey: PNFPYYUXIKTZMV-UHFFFAOYSA-N

物化性质

• 沸点：
  299.1±9.0 °C(Predicted)
• 密度：
  1.104±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-isopropylcinnamoyl chloride 在 PEG-400 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 3-(4-isopropylphenyl)-N-[N'-(2-thiophen-2-ylacetyl)hydrazinocarbothioyl]acrylamide
  参考文献：
  名称：

  A novel serine racemase inhibitor suppresses neuronal over-activation in vivo

  摘要：

  Serine racemase (SRR) is an enzyme that produces o-serine from L-serine. D-Serine acts as an endogenous coagonist of NMDA-type glutamate receptors (NMDARs), which regulate many physiological functions. Over-activation of NMDARs induces excitotoxicity, which is observed in many neurodegenerative disorders and epilepsy states. In our previous works on the generation of SRR gene knockout (Srr-KO) mice and its protective effects against NMDA- and A beta peptide-induced neurodegeneration, we hypothesized that the regulation of NMDARs' over-activation by inhibition of SRR activity is one such therapeutic strategy to combat these disease states. In the previous study, we performed in silico screening to identify four compounds with inhibitory activities against recombinant SRR. Here, we synthesized 21 derivatives of candidate 1, one of four hit compounds, and performed screening by in vitro evaluations. The derivative 13J showed a significantly lower IC50 value in vitro, and suppressed neuronal over-activation in vivo. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.05.011
• 作为产物：
  描述：

  4-异丙基肉硅酸 在 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 4-isopropylcinnamoyl chloride
  参考文献：
  名称：

  光诱导脱氨基 [3 + 2] 环化反应实现 γ-内酰胺的高度非对映选择性合成

  摘要：

  描述了用于合成官能化 γ-内酰胺的N-氨基吡啶鎓盐与烯烃的光引发脱氨基 [3 + 2] 环化反应。这种转变显示出良好的官能团耐受性以及出色的非对映选择性。初步研究表明，所采用的N-氨基吡啶鎓盐通过光诱导单电子转移 (SET) 过程通过 N-N 键断裂产生关键的酰胺基自由基中间体。酰胺基自由基物质将添加到烯烃的双键上，然后进行自由基介导的环化过程，以提供所需的 γ-内酰胺。

  DOI：

  10.1021/acs.orglett.2c01565

文献信息

• Syntheses and Biological Activities of Pyranyl-substituted Cinnamates
  作者：Jun ZHU、Motoji MAJIKINA、Shinkichi TAWATA

  DOI：10.1271/bbb.65.161

  日期：2001.1

  Twenty-two kinds of pyranyl-substituted cinnamates were synthesized by the reaction of 4-hydroxy-6-(2-phenylethyl)-2H-pyran-2-one or 4-hydroxy-6-methyl-2H-pyran-2-one (HMP) with a variety of substituted cinnamic acids, and their antifungal and plant growth inhibitory activities were investigated. Among the compounds prepared, 6-methyl-2-oxo-2H-pyran-4-yl 3-(4-isopropylphenyl)propenoate (H5) showed the strongest antifungal activity against Rhizoctonia solani and Sclerotium dellfinii, and 6-methyl-2-oxo-2H-pyran-4-yl3-(2-methylphenyl)propenoate (H2) had the highest plant gorwth inhibitory activity toward Brassica rapa.

  合成了二十二种吡喃基取代肉桂酸酯，通过4-羟基-6-(2-苯乙基)-2H-吡喃-2-酮或4-羟基-6-甲基-2H-吡喃-2-酮（HMP）与多种取代肉桂酸反应，并研究了它们的抗真菌和植物生长抑制活性。在所制备的化合物中，6-甲基-2-氧代-2H-吡喃-4-基-3-(4-异丙基苯基)丙烯酸酯（H5）对根腐病菌和斯克莱罗提尔病菌表现出最强的抗真菌活性，而6-甲基-2-氧代-2H-吡喃-4-基-3-(2-甲基苯基)丙烯酸酯（H2）则对油菜（Brassica rapa）具有最高的植物生长抑制活性。
• Structure based inhibitor design targeting glycogen phosphorylase b. Virtual screening, synthesis, biochemical and biological assessment of novel N-acyl-β-d-glucopyranosylamines
  作者：Vanessa Parmenopoulou、Anastassia L. Kantsadi、Vicky G. Tsirkone、Demetra S.M. Chatzileontiadou、Stella Manta、Spyros E. Zographos、Christina Molfeta、Georgios Archontis、Loranne Agius、Joseph M. Hayes、Demetres D. Leonidas、Dimitri Komiotis

  DOI：10.1016/j.bmc.2014.06.058

  日期：2014.9

  Glycogen phosphorylase (GP) is a validated target for the development of new type 2 diabetes treatments. Exploiting the Zinc docking database, we report the in silico screening of 1888 N-acyl-β-d-glucopyranosylamines putative GP inhibitors differing only in their R groups. CombiGlide and GOLD docking programs with different scoring functions were employed with the best performing methods combined in

  糖原磷酸化酶（GP）是开发新型2型糖尿病治疗方法的有效靶标。利用锌对接数据库，我们报告了1888 N-酰基-β- d的计算机筛选-葡萄糖吡喃糖胺假定的GP抑制剂仅在其R基团上有所不同。将具有不同评分功能的CombiGlide和GOLD对接程序与性能最佳的方法结合使用，以“共识评分”方法对活性位点的配体结合亲和力进行排名。然后合成了从筛选中选出的六种候选物，并在体外和离体中评估了它们的抑制能力。在体外，它们的抑制常数范围为5至377μM，而其中两个在低μM浓度下可有效导致大鼠肝细胞GP失活。定义了与抑制剂复合的GP的晶体结构，并为它们的抑制效能提供了结构基础，并为进一步基于结构的更有效抑制剂的设计提供了数据。
• Benzimidazole cyclooxygenase-2 inhibitors
  申请人：——

  公开号：US20030013886A1

  公开（公告）日：2003-01-16

  This invention provides a compound of the following formula: 1 Or the pharmaceutically acceptable salts thereof, wherein Ar is heteroaryl; X 1 and X 2 are independently selected from halo, C 1 -C 4 alkyl, hydroxy, C 1 -C 4 alkoxy, amino, C 1 -C 4 alkanoyl, carboxy, carbamoyl, cyano, nitro, mercapto, (C 1 -C 4 alkyl)thio, (C 1 -C 4 alkyl)sulfinyl, (C 1 -C 4 alkyl)sulfonyl, aminosulfonyl, or the like; R 1 is selected from hydrogen,. straight or branched C 1 -C 4 alkyl, C 3 -C 8 cycloalkyl, C 4 -C 8 cycloalkenyl, phenyl , heteroaryl and the like; R 2 and R 3 are independently selected from hydrogen, halo, C 1 -C 4 alkyl, phenyl and the like; or R 1 and R 2 can form, together with the carbon atom to which they are attached, a C 5 -C 7 cycloalkyl ring; and m and n are independently 0, 1, 2 or 3. These compounds and pharmaceutical compositions containing such compounds are useful as analgesics and anti-inflammatory agents.

  本发明提供以下式的化合物：1或其药学上可接受的盐，其中Ar是杂环芳基；X1和X2分别选自卤素，C1-C4烷基，羟基，C1-C4烷氧基，氨基，C1-C4酰基，羧基，氨基甲酰基，氰基，硝基，巯基，(C1-C4烷基)硫基，(C1-C4烷基)亚砜基，(C1-C4烷基)磺酰基，氨基磺酰基，或类似物；R1选自氢，直链或支链C1-C4烷基，C3-C8环烷基，C4-C8环烯基，苯基，杂环芳基等；R2和R3分别选自氢，卤素，C1-C4烷基，苯基等；或R1和R2可以与它们所连接的碳原子一起形成C5-C7环烷基环；m和n分别独立地为0、1、2或3。这些化合物和含有这些化合物的药物组合物在作为镇痛和抗炎药物方面是有用的。
• Benzimidazole cyclooxygenase-2 inhibitor
  申请人：Pfizer Inc

  公开号：US20040181062A1

  公开（公告）日：2004-09-16

  This invention provides a compound of the following formula: 1 or the pharmaceutically acceptable salts thereof, wherein Ar is heteroaryl; X 1 and X 2 are independently selected from halo, C 1 -C 4 alkyl, hydroxy, C 1 -C 4 alkoxy, amino, C 1 -C 4 alkanoyl, carboxy, carbamoyl, cyano, nitro, mercapto, (C 1 -C 4 alkyl)thio, (C 1 -C 4 alkyl)sulfinyl, (C 1 -C 4 alkyl)sulfonyl, aminosulfonyl, or the like; R 1 is selected from hydrogen, straight or branched C 1 -C 4 alkyl, C 3 -C 8 cycloalkyl, C 4 -C 8 cycloalkenyl, phenyl, heteroaryl and the like; R 2 and R 3 are independently selected from hydrogen, halo, C 1 -C 4 alkyl, phenyl and the like; or R 1 and R 2 can form, together with the carbon atom to which they are attached, a C 5 -C 7 cycloalkyl ring; and m and n are independently 0, 1, 2 or 3. These compounds and pharmaceutical compositions containing such compounds are useful as analgesics and anti-inflammatory agents.

  这项发明提供了以下公式的化合物：1或其药学上可接受的盐，其中Ar是杂环芳基；X1和X2独立选择自卤素，C1-C4烷基，羟基，C1-C4烷氧基，氨基，C1-C4酰基，羧基，氨基甲酰基，氰基，硝基，巯基，（C1-C4烷基）硫醇基，（C1-C4烷基）亚砜基，（C1-C4烷基）磺酰基，氨基磺酰基等；R1选择自氢，直链或支链C1-C4烷基，C3-C8环烷基，C4-C8环烯基，苯基，杂环芳基等；R2和R3独立选择自氢，卤素，C1-C4烷基，苯基等；或者R1和R2可以与它们所附着的碳原子一起形成C5-C7环烷基环；m和n独立选择自0、1、2或3。这些化合物和含有这些化合物的药物组合物可用作镇痛剂和抗炎剂。
• The design, synthesis and in vitro immunosuppressive evaluation of novel isobenzofuran derivatives
  作者：Na Yang、Qing-He Wang、Wen-Qian Wang、Jian Wang、Feng Li、Shen-Peng Tan、Mao-Sheng Cheng

  DOI：10.1016/j.bmcl.2011.11.078

  日期：2012.1

  The synthesis and biological evaluation of a series of novel isobenzofuran-based compounds are described. The compounds were evaluated for their immunosuppressive effects of T-cell proliferation and IMPDH type II inhibitor activity in vitro, as well as their structure-activity relationships were assessed. Several compounds demonstrated highly efficacious immunosuppressive properties, especially compounds 2d, 2e, 2h and 2j, which were superior to MPA, while compounds 2k, 2m, 2n, 4c and 5d exhibited an equipotent inhibitory activity compared to MPA. Generally, it was obviously demonstrated that alpha,beta-unsaturated amides proved more potent than the diamide and urea series. The present study provides a guide for further research on development of safe and effective immunosuppressive agents. (C) 2011 Elsevier Ltd. All rights reserved.