ethyl 2-(2-fluoro-4-nitrophenoxy)acetate | 805237-87-0

• 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 2-(2-fluoro-4-nitrophenoxy)acetate
• 英文别名: (2-fluoro-4-nitro-phenoxy)-acetic acid ethyl ester
• CAS: 805237-87-0
• 化学式: C₁₀H₁₀FNO₅
• mdl: MFCD11621702
• 分子量: 243.192
• InChiKey: ZUZIMRHYSJZLEV-UHFFFAOYSA-N

物化性质

• 沸点：
  358.4±27.0 °C(Predicted)
• 密度：
  1.332±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  81.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 2-(2-fluoro-4-nitrophenoxy)acetate 在 铁粉 、 氯化铵 作用下， 以 乙醇 、 水 为溶剂， 以57.1 %的产率得到ethyl 2-(4-amino-2-fluorophenoxy)acetate
  参考文献：
  名称：

  基于 Fedratinib 部分的 Janus 激酶 (JAK) 和组蛋白去乙酰化酶 (HDAC) 双特异性抑制剂的探索，用于治疗血液系统恶性肿瘤和实体癌

  摘要：

  Janus 激酶 (JAK)–STAT 通路的反馈激活导致实体癌对组蛋白脱乙酰酶 (HDAC) 抑制剂不敏感。在此，设计并合成了一系列基于 fedratinib 部分的新型 2-amino-4-phenylaminopyrimidine JAK/HDAC 双靶点抑制剂。其中，21和30在纳摩尔水平上有效抑制 HDAC3/6 和 JAK1/2，并且对 JAK2 对一组 76 种激酶表现出出色的选择性。21和30在血液恶性肿瘤和实体癌中表现出显着的抗增殖活性，这得到了 JAK-STAT 和 HDAC 通路阻断和促凋亡活性的认可。基于出色的血浆稳定性和口服生物利用度，21和30有效地抑制了HEL和A549异种移植模型的肿瘤生长。综上所述，上述结果证实了JAK/HDAC双靶点抑制剂为血液恶性肿瘤和实体癌的靶向治疗提供了有价值的线索。

  DOI：

  10.1021/acs.jmedchem.3c00036
• 作为产物：
  描述：

  2-氟-4-硝基苯酚 、 氯乙酸乙酯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 10.0h， 以65%的产率得到ethyl 2-(2-fluoro-4-nitrophenoxy)acetate
  参考文献：
  名称：

  The anti-invasive role of novel synthesized pyridazine hydrazide appended phenoxy acetic acid against neoplastic development targeting matrix metallo proteases

  摘要：

  Neoplastic metastasis is a major process where tumor cells migrate from the primary tumor and colonize at other parts of our body to form secondary tumor. Cancer incidences are rising and novel anti-neoplastic compounds with new mechanism of actions are essential for preventing cancer related deaths. In the current examination, a novel series of pyridazine analogues 6a-l was synthesized and evaluated against metastatic neoplastic cells. Experimental data postulated compound 6j has potential cytotoxic efficacy with prolonged activity against various cancer cells, including A549, HepG2, A498, CaSki and SiHa cells. Moreover, compound 6j arrests the A549 migration and invasions markedly by counteracting matrix metalloproteinase (MMP)-2 and MMP-9 expressions. Also, compound 6j proved its potentiality against Dalton's solid lymphoma progression in-vivo by abridging MVD and MMP expressions. Compound 6j interacts with MMP-2 and MMP-9 by H-bond in-silico, thereby down regulates the MMPs action in tumourigenesis. Altogether, we concluded that compound 6j down regulates MMP-2 and MMP-9 and thereby impairs metastatic cancer cell migration and invasions which can be translated into a potent anti-neoplastic agent.

  DOI：

  10.1016/j.biopha.2017.08.105

文献信息

• Aniline derivatives, their manufacture and use as pharmaceuticals
  申请人：——

  公开号：US20040248951A1

  公开（公告）日：2004-12-09

  This invention relates to compounds of the formula 1 wherein X is N and Y is S or O; or X is S or O and Y is N; R 1 is hydrogen or C 1-7 -alkyl; R 2 and R 3 independently from each other are selected from the group consisting of hydrogen, C 1-7 -alkyl and C 1-7 -alkoxy; R 4 , R 5 , R 6 , and R 7 independently from each other are selected from the group consisting of hydrogen, C 1-7 -alkyl, C 3-7 -cycloalkyl, halogen, C 1-7 -alkoxy, C 1-7 -alkyl-C 1-7 -alkoxy-C 1-7 -alkyl, C 2-7 -alkenyl, C 2-7 -alkinyl, fluoro-C 1-7 -alkyl and cyano; R 8 is selected from the group consisting of hydrogen, C 1-7 -alkyl, C 3-7 -cycloalkyl and fluoro-C 1-7 -alkyl; R 9 is selected from the group consisting of hydrogen, C 1-7 -alkyl, C 2-7 -alkinyl, C 3-7 -cycloalkyl and fluoro-C 1-7 -alkyl; R 10 is selected from the group consisting of hydrogen, C 1-7 -alkyl, C 2-7 -alkinyl, C 3-7 -cycloalkyl and fluoro-C 1-7 -alkyl; R 11 is aryl or heteroaryl; N is 0, 1 or 2; and all enantiomers and pharmaceutically acceptable salts and/or esters thereof and their use as PPAR activators.

  这项发明涉及以下式的化合物 1 其中 X为N，Y为S或O；或 X为S或O，Y为N； R 1 为氢或C 1-7 -烷基； R 2 和R 3 彼此独立地从氢、C 1-7 -烷基和C 1-7 -烷氧基组成的群中选择； R 4 、R 5 、R 6 和R 7 彼此独立地从氢、C 1-7 -烷基、C 3-7 -环烷基、卤素、C 1-7 -烷氧基、C 1-7 -烷基-C 1-7 -烷氧基-C 1-7 -烷基、C 2-7 -烯基、C 2-7 -炔基、氟代C 1-7 -烷基和氰基中选择； R 8 从氢、C 1-7 -烷基、C 3-7 -环烷基和氟代C 1-7 -烷基中选择； R 9 从氢、C 1-7 -烷基、C 2-7 -炔基、C 3-7 -环烷基和氟代C 1-7 -烷基中选择； R 10 从氢、C 1-7 -烷基、C 2-7 -炔基、C 3-7 -环烷基和氟代C 1-7 -烷基中选择； R 11 为芳基或杂环芳基； N为0、1或2； 以及所有对映体和药学上可接受的盐和/或酯以及它们作为PPAR激动剂的用途。
• Aniline derivatives, their manufacture and use as pharmaceutical agents
  申请人：Hoffmann-La Roche Inc.

  公开号：US07345067B2

  公开（公告）日：2008-03-18

  This invention relates to compounds of the formula wherein X is N and Y is S or O; or X is S or O and Y is N; R1 is hydrogen or C1-7-alkyl; R2 and R3 independently from each other are selected from the group consisting of hydrogen, C1-7-alkyl and C1-7-alkoxy; R4, R5, R6, and R7 independently from each other are selected from the group consisting of hydrogen, C1-7-alkyl, C3-7-cycloalkyl, halogen, C1-7-alkoxy, C1-7-alkyl-C1-7-alkoxy-C1-7-alkyl, C2-7-alkenyl, C2-7-alkinyl, fluoro-C1-7-alkyl and cyano; R8 is selected from the group consisting of hydrogen, C1-7-alkyl, C3-7-cycloalkyl and fluoro-C1-7-alkyl; R9 is selected from the group consisting of hydrogen, C1-7-alkyl, C2-7-alkinyl, C3-7-cycloalkyl and fluoro-C1-7-alkyl; R10 is selected from the group consisting of hydrogen, C1-7-alkyl, C2-7-alkinyl, C3-7-cycloalkyl and fluoro-C1-7-alkyl; R11 is aryl or heteroaryl; N is 0, 1 or 2; and all enantiomers and pharmaceutically acceptable salts and/or esters thereof and their use as PPAR activators.

  本发明涉及以下式子的化合物： 其中，X为N，Y为S或O；或X为S或O，Y为N； R1为氢或C1-7烷基； R2和R3分别独立地选自氢、C1-7烷基和C1-7烷氧基的群； R4、R5、R6和R7分别独立地选自氢、C1-7烷基、C3-7环烷基、卤素、C1-7烷氧基、C1-7烷基-C1-7烷氧基-C1-7烷基、C2-7烯基、C2-7炔基、氟代C1-7烷基和氰基的群； R8选自氢、C1-7烷基、C3-7环烷基和氟代C1-7烷基的群； R9选自氢、C1-7烷基、C2-7炔基、C3-7环烷基和氟代C1-7烷基的群； R10选自氢、C1-7烷基、C2-7炔基、C3-7环烷基和氟代C1-7烷基的群； R11为芳基或杂环芳基； N为0、1或2； 以及它们的所有对映体和药学上可接受的盐和/或酯，并用作PPAR激动剂。
• ANILINE DERIVATIVES
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP1636198A1

  公开（公告）日：2006-03-22
• NOVEL PHENOXUACETIC ACID DERIVATIVE, PREPARATION METHOD THEREFOR AND USES OF DERIVATIVE AS DRUG
  申请人：CHINA PHARMACEUTICAL UNIVERSITY

  公开号：US20210122704A1

  公开（公告）日：2021-04-29

  The present invention relates to a novel phenoxyacetic acid derivative represented by the general formula (I), preparation method thereof and use of a pharmaceutical composition containing the derivative in preparing a medicament for treating diabetes and metabolic syndrome. The phenoxyacetic acid derivatives have excellent in vivo hypoglycemic activity, which can be used for preventing or treating diabetes.
• US7345067B2
  申请人：——

  公开号：US7345067B2

  公开（公告）日：2008-03-18