4-(2,4-二氯苯基)-2,4-二氧丁酸 | 105356-70-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-(2,4-二氯苯基)-2,4-二氧丁酸
• 英文名称: 4-(2,4-Dichloro-phenyl)-2,4-dioxo-butyric acid
• 英文别名: 4-(2,4-dichlorophenyl)-2,4-dioxobutanoic acid
• CAS: 105356-70-5
• 化学式: C₁₀H₆Cl₂O₄
• 分子量: 261.061
• InChiKey: RKFICNZDWSKKRL-UHFFFAOYSA-N

物化性质

• 沸点：
  408.4±35.0 °C(Predicted)
• 密度：
  1.539±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  71.4
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2918300090

反应信息

• 作为反应物：
  描述：

  2-氨基苯酚 、 4-(2,4-二氯苯基)-2,4-二氧丁酸 以 二乙二醇 为溶剂， 反应 0.08h， 以97%的产率得到(Z)-3-(2-(2,4-dichlorophenyl)-2-oxoethylidene)-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-one
  参考文献：
  名称：

  Microwave-assisted One-pot Efficient Synthesis of Functionalized 2-Oxo-2-phenylethylidenes-linked 2-Oxobenzo[1,4]oxazines and 2-Oxoquino[1,4]oxalines: Synthetic Applications, Antioxidant Activity, SAR and Cytotoxic Studies

  摘要：

  A microwave-assisted, environmentally benign green protocol for the synthesis of functionalized (Z)-3-(2-oxo-2- phenylethylidene)-3, 4-dihydro-2H-benzo[b][1,4] oxazin-2-ones (11a-n) in excellent yields (upto 97%) and (Z)-3-(2-oxo-2-phenylethylidene)-3,4-dihydroquinoxalin-2(1H)-ones (14a-h) (upto 96% yield) are reported. The practical applicability of developed methodology were also confirmed by the gram scale synthesis of 11a, 14c and 14e; synthesis of anticancer alkaloid Cephalandole A 16 (89% yield). All the synthesized compounds 11a-n, 14a-h and 16 were assessed for their in vitro antioxidant activities in DPPH radical scavenging and FRAP assay. In DPPH assay, compounds 11a, 14c and 14e, the most active compounds of the series, were found to show IC50 value of 10.20 +/- 0.08 mu g/mL, 9.89 +/- 0.15 mu g/mL and 8.97 +/- 0.13 mu g/mL, respectively in comparison with standard reference (ascorbic acid, IC50 = 4.57 mu g/mL). Whereas, in FRAP antioxidant assay seven compounds (11c, 11e, 11i, 11k, 11l, 14d and 14h) displayed higher antioxidant activity in comparison to the reference standard BHT (C-0.5 FRAP = 546.2 mu M). Moreover, the cytotoxic studies of the compounds 11a, 14c, 14e and 14h were found to be non-toxic in nature in 3T(3) fibroblast cell lines using MTT assay.

  DOI：

  10.17344/acsi.2017.3709
• 作为产物：
  描述：

  4-(2,4-二氯-苯基)-2,4-二羰基-丁酸甲基酯 在 lithium hydroxide monohydrate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 生成 4-(2,4-二氯苯基)-2,4-二氧丁酸
  参考文献：
  名称：

  非肽类新型血小板聚集抑制剂：设计、合成、生物评价、SAR 和计算机研究

  摘要：

  一系列 2-oxo-2-phenylethylidene 连接的 2-oxo-benzo[1,4]oxazine 类似物 17a-x 和 18a-o，在环 A 和环 C，在更环保的条件下以优异的产率（高达 98%）合成。与标准参考阿司匹林 (IC50 = 21.34 ± 1.09 µg/mL) 相比，评估了这些类似物 17a-x 和 18a-o 的花生四烯酸 (AA) 诱导的血小板聚集抑制活性。在所有筛选的化合物中，与阿司匹林相比，8 种类似物 17i、17x、18f、18g、18h、18i、18l 和 18o 被鉴定为有前途的血小板聚集抑制剂。此外，通过 MTT 分析对 3T3 成纤维细胞系进行了有希望的化合物（17i、17x、18f-18i、18l、和 18o) 并且发现这些化合物在性质上是无毒的。此外，这些化合物（17i、17x、18f-18i、18l 和 18o）的 AA 诱导的血

  DOI：

  10.1002/ardp.201700349

文献信息

• “On water” ultrasound-assisted one pot efficient synthesis of functionalized 2-oxo-benzo[1,4]oxazines: First application to the synthesis of anticancer indole alkaloid, Cephalandole A
  作者：Pradeep K. Jaiswal、Vashundhra Sharma、Jaroslav Prikhodko、Irina V. Mashevskaya、Sandeep Chaudhary

  DOI：10.1016/j.tetlet.2017.03.048

  日期：2017.5

  For the first time, an efficient, simple, synthetic green protocol for the one-pot synthesis of functionalized 2-oxo-benzo[1,4]oxazines 24–29 in water under ultrasound irradiation is presented. As compared to conventional methods, the present protocol avoids traditional chromatography and purification steps and furnished the target molecules in excellent yields (upto 98%) with no side products. The

  对于第一次，一个高效，简便的，合成的绿协议的一锅合成官能-2-氧代苯并[1,4]恶嗪24 - 29在超声照射下的水被呈现。与常规方法相比，本方案避免了传统的色谱和纯化步骤，并以极高的收率（高达98％）提供了目标分子，且没有副产物。该方法也已在克级合成中得到证明。此外，官能化2-氧代-喹喔啉类似物31 - 33，另一类生物活性杂环支架的，使用这种方法，还制备。该方案首次成功地用于抗癌吲哚生物碱Cephalandole A的合成35。
• The identification and optimization of 2,4-diketobutyric acids as flap endonuclease 1 inhibitors
  作者：L. Nathan Tumey、Bayard Huck、Elizabeth Gleason、Jianmin Wang、Daniel Silver、Kurt Brunden、Sherry Boozer、Stephen Rundlett、Bruce Sherf、Steven Murphy、Andrew Bailey、Tom Dent、Christina Leventhal、John Harrington、Youssef L. Bennani

  DOI：10.1016/j.bmcl.2004.07.028

  日期：2004.10

  There have been several recent reports of chemopotentiation via inhibition of DNA repair processes. Flap endonuclease 1 (FEN1) is a key enzyme involved in base excision repair (BER), a primary pathway utilized by mammalian cells to repair DNA damage. In this report, we describe the identification and SAR of a series of 2,4-diketobutyric acid FENI inhibitors. (C) 2004 Elsevier Ltd. All rights reserved.
• Non-peptide-based new class of platelet aggregation inhibitors: Design, synthesis, bioevaluation, SAR, and<i>in silico</i>studies
  作者：Pradeep K. Jaiswal、Vashundhra Sharma、Surendra Kumar、Manas Mathur、Ajit K. Swami、Dharmendra K. Yadav、Sandeep Chaudhary

  DOI：10.1002/ardp.201700349

  日期：2018.4

  A series of 2‐oxo‐2‐phenylethylidene linked 2‐oxo‐benzo[1,4]oxazine analogues 17a–x and 18a–o, incorporated with a variety of electron‐withdrawing as well as electron‐donating groups at ring A and ring C, were synthesized under greener conditions in excellent yields (up to 98%). These analogues 17a–x and 18a–o were evaluated for their arachidonic acid (AA)‐induced platelet aggregation inhibitory activities

  一系列 2-oxo-2-phenylethylidene 连接的 2-oxo-benzo[1,4]oxazine 类似物 17a-x 和 18a-o，在环 A 和环 C，在更环保的条件下以优异的产率（高达 98%）合成。与标准参考阿司匹林 (IC50 = 21.34 ± 1.09 µg/mL) 相比，评估了这些类似物 17a-x 和 18a-o 的花生四烯酸 (AA) 诱导的血小板聚集抑制活性。在所有筛选的化合物中，与阿司匹林相比，8 种类似物 17i、17x、18f、18g、18h、18i、18l 和 18o 被鉴定为有前途的血小板聚集抑制剂。此外，通过 MTT 分析对 3T3 成纤维细胞系进行了有希望的化合物（17i、17x、18f-18i、18l、和 18o) 并且发现这些化合物在性质上是无毒的。此外，这些化合物（17i、17x、18f-18i、18l 和 18o）的 AA 诱导的血
• Microwave-assisted One-pot Efficient Synthesis of Functionalized 2-Oxo-2-phenylethylidenes-linked 2-Oxobenzo[1,4]oxazines and 2-Oxoquino[1,4]oxalines: Synthetic Applications, Antioxidant Activity, SAR and Cytotoxic Studies
  作者：Vashundhra Sharma、Pradeep K. Jaiswal、Dharmendra K. Yadav、Mukesh Saran、Jaroslav Prikhodko、Manas Mathur、Ajit K. Swami、Irina V. Mashevskaya、Sandeep Chaudhary

  DOI：10.17344/acsi.2017.3709

  日期：2017.12.15

  A microwave-assisted, environmentally benign green protocol for the synthesis of functionalized (Z)-3-(2-oxo-2- phenylethylidene)-3, 4-dihydro-2H-benzo[b][1,4] oxazin-2-ones (11a-n) in excellent yields (upto 97%) and (Z)-3-(2-oxo-2-phenylethylidene)-3,4-dihydroquinoxalin-2(1H)-ones (14a-h) (upto 96% yield) are reported. The practical applicability of developed methodology were also confirmed by the gram scale synthesis of 11a, 14c and 14e; synthesis of anticancer alkaloid Cephalandole A 16 (89% yield). All the synthesized compounds 11a-n, 14a-h and 16 were assessed for their in vitro antioxidant activities in DPPH radical scavenging and FRAP assay. In DPPH assay, compounds 11a, 14c and 14e, the most active compounds of the series, were found to show IC50 value of 10.20 +/- 0.08 mu g/mL, 9.89 +/- 0.15 mu g/mL and 8.97 +/- 0.13 mu g/mL, respectively in comparison with standard reference (ascorbic acid, IC50 = 4.57 mu g/mL). Whereas, in FRAP antioxidant assay seven compounds (11c, 11e, 11i, 11k, 11l, 14d and 14h) displayed higher antioxidant activity in comparison to the reference standard BHT (C-0.5 FRAP = 546.2 mu M). Moreover, the cytotoxic studies of the compounds 11a, 14c, 14e and 14h were found to be non-toxic in nature in 3T(3) fibroblast cell lines using MTT assay.