ethyl 3-(dimethylamino)-1-(4'-methylphenyl)-prop-2-enone-2-carboxylate | 76344-77-9

• 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: ethyl 3-(dimethylamino)-1-(4'-methylphenyl)-prop-2-enone-2-carboxylate
• 英文别名: ethyl 1-(4'-methylphenyl)-3-(dimethylamino)prop-2-enone-2-carboxylate；3-dimethylamino-2-(4-methyl-benzoyl)-acrylic acid ethyl ester；ethyl 3-(dimethylamino)-2-(4-methylbenzoyl)prop-2-enoate
• CAS: 76344-77-9
• 化学式: C₁₅H₁₉NO₃
• 分子量: 261.321
• InChiKey: RRCBCGPTBNSMKE-UHFFFAOYSA-N

物化性质

• 沸点：
  138-143 °C(Press: 3 Torr)
• 密度：
  1.086±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 3-(dimethylamino)-1-(4'-methylphenyl)-prop-2-enone-2-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 26.0h， 生成
  参考文献：
  名称：

  4-Substituted 1,5-diarylpyrazole, analogues of celecoxib: synthesis and preliminary evaluation of biological properties

  摘要：

  A number of 5-aryl-1-[4-(methylsulfonyl)-phenyl]-1H-pyrazoles and 4-(5-aryl-1H-pyrazol-1-yl)benzenesulfonamides 3, 4, 5, 6, analogues of the COX-2 selective inhibitor celecoxib (celebrex), were synthesized. In order to verify the effects on the biological properties of certain substituents put on position 4 of the pyrazole nucleus, some of these compounds were screened in vivo for their anti-inflammatory and analgesic activities. Moreover, sodium salts of carboxylic acids 4 were tested in vitro for their platelet anti-aggregating properties. The results of these preliminary biological assays showed that new derivatives are not endowed with improved anti-inflammatory and analgesic properties, in comparison with celecoxib. In addition, docking studies were carried out on the most significative compounds to evaluate their interaction mode at the active site of both COX-1 and COX-2. Some remarks about the SAR of this class of COX-inhibitors are drown out.

  DOI：

  10.1016/s0014-827x(03)00136-8
• 作为产物：
  描述：

  对甲基苯甲酸乙酯 在 sodium hydride 作用下， 以 苯 为溶剂， 反应 5.0h， 生成 ethyl 3-(dimethylamino)-1-(4'-methylphenyl)-prop-2-enone-2-carboxylate
  参考文献：
  名称：

  4-Substituted 1,5-diarylpyrazole, analogues of celecoxib: synthesis and preliminary evaluation of biological properties

  摘要：

  A number of 5-aryl-1-[4-(methylsulfonyl)-phenyl]-1H-pyrazoles and 4-(5-aryl-1H-pyrazol-1-yl)benzenesulfonamides 3, 4, 5, 6, analogues of the COX-2 selective inhibitor celecoxib (celebrex), were synthesized. In order to verify the effects on the biological properties of certain substituents put on position 4 of the pyrazole nucleus, some of these compounds were screened in vivo for their anti-inflammatory and analgesic activities. Moreover, sodium salts of carboxylic acids 4 were tested in vitro for their platelet anti-aggregating properties. The results of these preliminary biological assays showed that new derivatives are not endowed with improved anti-inflammatory and analgesic properties, in comparison with celecoxib. In addition, docking studies were carried out on the most significative compounds to evaluate their interaction mode at the active site of both COX-1 and COX-2. Some remarks about the SAR of this class of COX-inhibitors are drown out.

  DOI：

  10.1016/s0014-827x(03)00136-8

文献信息

• PYRIMIDINE COMPOUNDS AS SEROTONIN RECEPTOR MODULATORS
  申请人：Dvorak A. Curt

  公开号：US20070032481A1

  公开（公告）日：2007-02-08

  Certain pyrimidine-containing compounds are serotonin receptor modulators useful in the treatment of serotonin-mediated diseases.

  某些含嘧啶的化合物是有效的血清素受体调节剂，可用于治疗血清素介导的疾病。
• Synthesis and Cytotoxicity of Substituted Ethyl 2-Phenacyl-3-phenylpyrrole-4-carboxylates
  作者：Michael A. Evans、Daniel C. Smith、Justin M. Holub、Anthony Argenti、Mafoloe Hoff、Gerard A. Dalglish、Donna L. Wilson、Brett M. Taylor、Joshua D. Berkowitz、Bruce S. Burnham、Keith Krumpe、John T. Gupton、Tanya C. Scarlett、Richard W. Durham, Jr、Iris H. Hall

  DOI：10.1002/ardp.200390018

  日期：2003.6

  The substituted ethyl‐2‐phenacyl‐3‐phenylpyrrole‐4‐carboxylates were synthesized by a condensation of a beta‐chloroenal and an alpha‐aminoketone under neutral conditions. They proved to be potent cytotoxic agents against the growth of murine L1210 and P388 leukemias and human HL‐60 promyelocytic leukemia, HuT‐78 lymphoma, and HeLa‐S3 uterine carcinoma. Selective compounds were active against the growth

  取代的乙基-2-苯甲酰基-3-苯基吡咯-4-羧酸酯是通过β-氯烯醛和α-氨基酮在中性条件下缩合合成的。它们被证明是针对鼠 L1210 和 P388 白血病以及人 HL-60 早幼粒细胞白血病、HuT-78 淋巴瘤和 HeLa-S3 子宫癌生长的有效细胞毒剂。选择性化合物对 Tmolt3 和 Tmolt4 白血病和 THP-1 急性单核细胞白血病、肝 Hepe-2、卵巢 1-A9、回肠 HCT-8 腺癌和骨肉瘤 HSO 的生长具有活性。HL-60 细胞的作用模式研究表明，DNA 和蛋白质合成在 100 [TH] μM 下 60 [TH] 分钟后受到抑制。DNA 和 RNA 聚合酶、PRPP-酰胺基转移酶、二氢叶酸还原酶、胸苷酸合酶、和 TMP 激酶活性受到试剂的干扰，d [NTP] 池减少。与 DNA 碱基的非特异性相互作用和 DNA 的交联可能在这些羧酸盐的作用模式中起作用。
• Rational design, synthesis and biological evaluation of new 1,5-diarylpyrazole derivatives as CB1 receptor antagonists, structurally related to rimonabant
  作者：Giulia Menozzi、Paola Fossa、Elena Cichero、Andrea Spallarossa、Angelo Ranise、Luisa Mosti

  DOI：10.1016/j.ejmech.2008.01.043

  日期：2008.12

  4-dichlorophenyl)-5-arylpyrazoles strictly related to rimonabant, but with the hydrazide/amide group shifted from position 3 to position 4 of the pyrazole scaffold. The synthesized compounds were evaluated in vitro for their affinity on human CB(1) and CB(2) (cannabinoid type-2) receptors. Computational studies, performed both in the design step and after biological assays, contributed to rationalize the obtained

  在1型大麻素（CB（1））受体拮抗剂中，围绕利莫那班（Acomplia）的1,5-二芳基吡唑骨架开发的那些拮抗剂（对Acomplia进行了最广泛的研究。近年来，有关该主题的许多SAR和QSAR报告已经发表，着眼于N1和C5芳基官能团的取代和取向以及3-羧酰胺位置的取代基在这种情况下，我们的研究目的是设计和合成一组1-（2,4-二氯苯基） -5-芳基吡唑与利莫那班严格相关，但酰肼/酰胺基团从吡唑支架的3位转移到4位。合成后的化合物在体外对人CB（1）和CB（2）的亲和力进行了评估（大麻素2型受体）在设计步骤和生物学分析后均进行了计算研究，在拮抗剂和人类CB（1）受体之间的特定分子相互作用方面，有助于合理化所获得的结果。
• Pyrimidine compounds as serotonin receptor modulators
  申请人：Janssen Pharmaceutica NV

  公开号：US07598255B2

  公开（公告）日：2009-10-06

  Certain pyrimidine-containing compounds are serotonin receptor modulators useful in the treatment of serotonin-mediated diseases.

  某些含嘧啶的化合物是血清素受体调节剂，可用于治疗与血清素相关的疾病。
• Holub, Justin M.; O'Toole-Colin, Kathy; Getzel, Adam, Molecules, 2004, vol. 9, # 3, p. 135 - 157
  作者：Holub, Justin M.、O'Toole-Colin, Kathy、Getzel, Adam、Argenti, Anthony、Evans, Michael A.、Smith, Daniel C.、Dalglish, Gerard A.、Rifat, Shahzad、Wilson, Donna L.、Taylor, Brett M.、Miott, Ulander、et al.

  DOI：——

  日期：——