3-(4-氟-苯基)-1-甲基-1H-吡唑-4-甲醛 | 689250-53-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 3-(4-氟-苯基)-1-甲基-1H-吡唑-4-甲醛
• 英文名称: 3-(4-fluorophenyl)-1-methyl-1H-pyrazole-4-carbaldehyde
• 英文别名: 3-(4-fluorophenyl)-1-methylpyrazole-4-carbaldehyde
• CAS: 689250-53-1
• 化学式: C₁₁H₉FN₂O
• mdl: MFCD11053200
• 分子量: 204.204
• InChiKey: FDGWWNFZSAQDAN-UHFFFAOYSA-N

物化性质

• 沸点：
  353.1±32.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933199090

反应信息

• 作为反应物：
  描述：

  3-(4-氟-苯基)-1-甲基-1H-吡唑-4-甲醛 、 1,10-邻二氮杂菲-5,6-二酮 在 ammonium acetate 、 溶剂黄146 作用下， 反应 6.0h， 以85.3%的产率得到2-(3-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl)-1H-imidazo[4,5-f][1,10]phenanthroline
  参考文献：
  名称：

  Synthesis and the interaction of 2-(1 H -pyrazol-4-yl)-1 H -imidazo[4,5-f][1,10]phenanthrolines with telomeric DNA as lung cancer inhibitors

  摘要：

  A novel series of 2-(1H-pyrazol-4-y1)-1H-imidazo[4,5-f][1,101phenanthrolines were designed, synthesized and evaluated for their antitumor activity against lung adenocarcinoma by CCK-8 assay, electrophoretic mobility shift assay (EMSA), UV-melting study, wound healing assay and docking study. These compounds showed good inhibitory activities against lung adenocarcinoma. Especially compound 12c exhibited potential antiproliferative activity against A549 cell line with the half maximal inhibitory concentration (IC50) value of 1.48 mu M, which was a more potent inhibitor than cisplatin (IC50 = 12.08 mu M) and leading compound 2 (IC50 = 1.69 mu M), and the maximum cell inhibitory rate being up to 98.40%. Moreover, further experiments demonstrated that compounds 12a-d can strongly interact with telomeric DNA to stabilize G-quadruplex DNA with increased am values from 12.44 to 20.54 degrees C at a ratio of DNA to compound 1:10. These results implied that growth inhibition of A549 cells mediated by these phenanthroline derivatives is possibly positively correlated to the fact their interaction with telomeric G-quadruplexs. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.03.030
• 作为产物：
  描述：

  {[1-(4-Fluorophenyl)ethylidene]amino}urea 在 potassium carbonate 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3-(4-氟-苯基)-1-甲基-1H-吡唑-4-甲醛
  参考文献：
  名称：

  Synthesis and the interaction of 2-(1 H -pyrazol-4-yl)-1 H -imidazo[4,5-f][1,10]phenanthrolines with telomeric DNA as lung cancer inhibitors

  摘要：

  A novel series of 2-(1H-pyrazol-4-y1)-1H-imidazo[4,5-f][1,101phenanthrolines were designed, synthesized and evaluated for their antitumor activity against lung adenocarcinoma by CCK-8 assay, electrophoretic mobility shift assay (EMSA), UV-melting study, wound healing assay and docking study. These compounds showed good inhibitory activities against lung adenocarcinoma. Especially compound 12c exhibited potential antiproliferative activity against A549 cell line with the half maximal inhibitory concentration (IC50) value of 1.48 mu M, which was a more potent inhibitor than cisplatin (IC50 = 12.08 mu M) and leading compound 2 (IC50 = 1.69 mu M), and the maximum cell inhibitory rate being up to 98.40%. Moreover, further experiments demonstrated that compounds 12a-d can strongly interact with telomeric DNA to stabilize G-quadruplex DNA with increased am values from 12.44 to 20.54 degrees C at a ratio of DNA to compound 1:10. These results implied that growth inhibition of A549 cells mediated by these phenanthroline derivatives is possibly positively correlated to the fact their interaction with telomeric G-quadruplexs. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.03.030

文献信息

• [EN] AGENT FOR PREVENTING OR TREATING NEUROPATHY<br/>[FR] AGENT POUR LA PRÉVENTION OU LE TRAITEMENT DE NEUROPATHIE
  申请人：TAKEDA CHEMICAL INDUSTRIES LTD

  公开号：WO2004039365A1

  公开（公告）日：2004-05-13

  The present invention provides an agent for preventing or treating neuropathy having superior action and low toxicity. This agent comprises a compound represented by the formula:wherein ring A is a 5-membered aromatic heterocycle containing 2 or more nitrogen atoms, which may further have substituent(s);B is an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group;X is a divalent acyclic hydrocarbon group;Z is -O-, -S-, -NR2-, -CONR2- or -NR2CO- (R2 is a hydrogen atom or an optionally substituted alkyl group);Y is a bond or a divalent acyclic hydrocarbon group;R1 is an optionally substituted cyclic group, an optionally substituted amino group or an optionally substituted acyl group, provided that when the 5-membered aromatic heterocycle represented by ring A is imidazole, then Z should not be -O-, or a salt thereof.

  本发明提供了一种具有优越作用和低毒性的预防或治疗神经病的药剂。该药剂包括一个由以下式表示的化合物：其中环A是含有2个或更多氮原子的5元芳香杂环，可能进一步具有取代基；B是一个可选择取代的碳氢基团或可选择取代的杂环基团；X是二价的无环碳氢基团；Z是-O-，-S-，-NR2-，-CONR2-或-NR2CO-（R2是氢原子或可选择取代的烷基基团）；Y是键或二价的无环碳氢基团；R1是可选择取代的环基团，可选择取代的氨基团或可选择取代的酰基团，但当环A表示的5元芳香杂环是咪唑时，Z不应为-O-，或其盐。
• Agent for preventing or treating neuropathy
  申请人：Momose Yu

  公开号：US20060004069A1

  公开（公告）日：2006-01-05

  The present invention provides an agent for preventing or treating neuropathy having superior action and low toxicity. This agent comprises a compound represented by the formula: wherein ring A is a 5-membered aromatic heterocycle containing 2 or more nitrogen atoms, which may further have substituent(s); B is an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group; X is a divalent acyclic hydrocarbon group; Z is —O—, —S—, —NR 2 —, —CONR 2 — or —NR 2 CO— (R 2 is a hydrogen atom or an optionally substituted alkyl group); Y is a bond or a divalent acyclic hydrocarbon group; R 1 is an optionally substituted cyclic group, an optionally substituted amino group or an optionally substituted acyl group, provided that when the 5-membered aromatic heterocycle represented by ring A is imidazole, then Z should not be —O—, or a salt thereof.

  本发明提供了一种用于预防或治疗神经病的药剂，具有优异的作用和低毒性。该药剂包括以下式子所表示的化合物：其中环A是一个含有2个或更多氮原子的5元芳香杂环，可以进一步具有取代基；B是一个可选取代的碳氢化合物基团或可选取代的杂环基团；X是一个二价的无环碳氢基团；Z是—O—、—S—、—NR2—、—CONR2—或—NR2CO—（其中R2是氢原子或可选取代的烷基基团）；Y是一个键或一个二价的无环碳氢基团；R1是一个可选取代的环基、可选取代的氨基或可选取代的酰基，但当环A所表示的5元芳香杂环是咪唑时，Z不应为—O—，或其盐。
• Structure–activity relationship study of a novel necroptosis inhibitor, necrostatin-7
  作者：Weihong Zheng、Alexei Degterev、Emily Hsu、Junying Yuan、Chengye Yuan

  DOI：10.1016/j.bmcl.2008.08.058

  日期：2008.9

  Necroptosis is a regulated caspase-independent cell death mechanism characterized by morphological features resembling non-regulated necrosis. Necrotatin-7 (Nec-7), a novel potent small-molecule inhibitor of necroptosis, is structurally distinct from previously described necrostatins (Nec-1, Nec-3, Nec-4 and Nec-5). Here, we describe a series of structural modi. cations and the structure-activity relationship (SAR) of the Nec-7 series for inhibiting necroptosis. (C) 2008 Elsevier Ltd. All rights reserved.
• AGENT FOR PREVENTING OR TREATING NEUROPATHY
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP1556032A1

  公开（公告）日：2005-07-27
• PREPARATION AND METHODS OF USE FOR ORTHO-ARYL 5-MEMBERED HETEROARYL-CARBOXAMIDE CONTAINING MULTI-TARGETED KINASE INHIBITORS
  申请人：Spacefill Enterprises LLC

  公开号：US20180125848A1

  公开（公告）日：2018-05-10

  The present disclosure relates to compounds of the Formula (I): and pharmaceutically acceptable salts, as kinase modulators, compatible with the Type-II inhibition of kinases.