(E)-ethyl 2-methyl-3-(3-nitrophenyl)acrylate | 119870-76-7

• 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: (E)-ethyl 2-methyl-3-(3-nitrophenyl)acrylate
• 英文别名: 2-methyl-3t-(3-nitro-phenyl)-acrylic acid ethyl ester；2-Methyl-3t-(3-nitro-phenyl)-acrylsaeure-aethylester；Ethyl 2-Methyl-3-(3-Nitrophenyl)propenoate；ethyl (E)-2-methyl-3-(3-nitrophenyl)prop-2-enoate
• CAS: 119870-76-7
• 化学式: C₁₂H₁₃NO₄
• 分子量: 235.24
• InChiKey: OBKAGLKKBXFHKX-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-ethyl 2-methyl-3-(3-nitrophenyl)acrylate 在 铁粉 、 氯化铵 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成
  参考文献：
  名称：

  Design and Synthesis of Small Molecule RhoA Inhibitors: A New Promising Therapy for Cardiovascular Diseases?

  摘要：

  RhoA is a member of Rho GTPases, a subgroup of the Ras superfamily of small GTP-binding proteins. RhoA, as important regulator of diverse cellular signaling pathways, plays significant roles in cytoskeletal organization, transcription, and cell-cycle progression. The RhoA/ROCK inhibitors have emerged as a new promising treatment for cardiovascular diseases. However, to date, RhoA inhibitors are macromolecules, and to our knowledge, small molecular-based inhibitors have not been reported. In this study, a series of first-in-class small molecular RhoA inhibitors have been discovered by using structure-based virtual screening in conjunction with chemical synthesis and bioassay. Virtual screening of similar to 200,000 compounds, followed by SPR-based binding affinity assays resulted in three compounds with binding affinities to RhoA at the micromolar level (compounds 1-3). Compound 1 was selected for further structure modifications in considering binding activity and synthesis ease. Fourty-one new compounds (1, 12a-v, 13a-h, and 14a-j) were designed and synthesized accordingly. It was found that eight (12a, 12j, 14a, 14b, 14d, 14e, 14 g, and 14h) showed high RhoA inhibition activities with IC(50) values of 1.24 to 3.00 mu M. A pharmacological assay indicated that two compounds (14g and 14 h) demonstrated noticeable vasorelaxation effects against PE-induced contraction in thoracic aorta artery rings and served as good leads for developing more potent cardiovascular agents.

  DOI：

  10.1021/jm200161c
• 作为产物：
  描述：

  2-(3-硝基羟基苄基)丙烯酸乙酯 在 三(五氟苯基)硼烷 polymethylhydrosiloxane 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以81%的产率得到(E)-ethyl 2-methyl-3-(3-nitrophenyl)acrylate
  参考文献：
  名称：

  Synthesis of trisubstituted alkenes by reductive dehydroxylation of Baylis–Hillman adducts using polymethylhydrosiloxane (PMHS) and catalytic B(C6F5)3

  摘要：

  B(C6F5)(3) as a catalyst and polymethylhydrosiloxane as a hydride source have been employed for the reductive dehydroxylation of Baylis-Hillman adducts wherein the hydride adds in an S(N)2' manner onto the unactivated allyl alcohol moiety with concomitant elimination of the hydroxy group along with double bond migration. The products formed were found to be E in the case of ester adducts and Z in the case of nitrile adducts. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.03.014

文献信息

• Carboxamide compounds as SRS-A antagonists, pharmaceutical compositions containing them, processes for the preparation, and intermediates useful therein
  申请人：PFIZER INC.

  公开号：EP0047119A1

  公开（公告）日：1982-03-10

  1.Carboxamide compounds of the formula and their pharmaceutically-acceptable salts; wherein R1 as hydrogen, alkyl having 1 to 4 carbon atoms or a group of the formula -CH2-CH2-NR3R4 wherein R3 and R4 are each alkyl having 1 to 3 carbon atoms; R2 is alkyl having 8 to 15 carbon atoms or cyclo-alkyl having from 6 to 12 carbon atoms; and Q is or wherein R5 and R6 are each hydrogen or methyl; with the proviso that when Q is I , the two groups attached to the group have a trans relationship to each other, pharmaceutical compositions containing them, processes for their preparation, and intermediates useful therein. The compounds of the formula (I) are SRS-A antagonists useful in such disease states as allergic rhinitis, certain skin disorders, and allergic bronchial asthma.

  1.式中的甲酰胺化合物 及其药学上可接受的盐类； 其中 R1 为氢、具有 1 至 4 个碳原子的烷基或式 -CH2-CH2-NR3R4 的基团，其中 R3 和 R4 各为具有 1 至 3 个碳原子的烷基； R2 是具有 8 至 15 个碳原子的烷基或具有 6 至 12 个碳原子的环烷基； Q 是 或 其中 R5 和 R6 分别为氢或甲基； 但当 Q 为 I 时，连接到该基团上的两个基团 式(I)化合物是 SRS-A 拮抗剂，可用于上述领域。式（I）化合物是 SRS-A 拮抗剂，可用于过敏性鼻炎、某些皮肤病和过敏性支气管哮喘等疾病。
• Carboxamide compounds as SRS-A antagonists and a process for producing same
  申请人：PFIZER INC.

  公开号：EP0050977A1

  公开（公告）日：1982-05-05

  The compounds of the invention are certain new pro- penamides and 2-butenamides having a (carboxyalkanami- do)phenyl or a (carboxyalkenamido)phenyl group at the 3-position, and certain esters thereof, and certain cyclopropanecarboxamide compounds having a (carboxyalkanami- do)phenyl group or a (carboxyalkenamido)phenyl group at the 2-position, and certain esters thereof. The compounds are useful for antagonizing the spasmogenic activity of slow-reacting substance of anaphylaxis (SRS-A) in a human subject. In particular, the compounds of the invention are useful for preventing and treating certain obstructive airways diseases, notably allergic bronchial asthma, allergic rhinitis and certain skin disorders, in human subjects.

  本发明的化合物是某些新的原戊酰胺类和 2-丁烯酰胺类化合物，它们在 3-位上具有(羧基烷酰胺基)苯基或(羧基烯酰胺基)苯基，及其某些酯类，以及某些在 2-位上具有(羧基烷酰胺基)苯基或(羧基烯酰胺基)苯基的环丙烷甲酰胺类化合物，及其某些酯类。 这些化合物可用于拮抗人体内的过敏性休克慢反应物质（SRS-A）的致痉活性。 特别是，本发明的化合物可用于预防和治疗人体内的某些阻塞性气道疾病，尤其是过敏性支气管哮喘、过敏性鼻炎和某些皮肤病。
• STUDY OF THE POSSIBLE ISOMERISM OF CERTAIN ANALOGS OF RESOLVABLE DIPHENYL COMPOUNDS. VII¹
  作者：R. W. Maxwell、Roger Adams

  DOI：10.1021/ja01370a059

  日期：1930.7
• US4296120A
  申请人：——

  公开号：US4296120A

  公开（公告）日：1981-10-20
• US4296129A
  申请人：——

  公开号：US4296129A

  公开（公告）日：1981-10-20