3-methyl-4-(4-nitrophenyl)-4,5-dihydro-1H-pyrazolo[3,4-b]pyridine-6(7H)-one | 442652-80-4

• 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: 3-methyl-4-(4-nitrophenyl)-4,5-dihydro-1H-pyrazolo[3,4-b]pyridine-6(7H)-one
• 英文别名: 4,5-dihydro-3-methyl-4-(4-nitrophenyl)-1H-pyrazolo[3,4-b]pyridin-6(7H)-one；3-methyl-4-(4-nitrophenyl)-1,2,4,5-tetrahydropyrazolo[3,4-b]pyridin-6-one
• CAS: 442652-80-4；937389-24-7
• 化学式: C₁₃H₁₂N₄O₃
• 分子量: 272.263
• InChiKey: QVIKMFNCGQXEHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.75
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  104.41
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-methyl-4-(4-nitrophenyl)-4,5-dihydro-1H-pyrazolo[3,4-b]pyridine-6(7H)-one 在 苯膦酰二氯 、 N,O-双(三甲基硅烷基)三氟乙酰胺 、 一水合肼 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 锌 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 4.0h， 生成 4-(3-methyl-1H-pyrazolo[3,4-b]pyridin-4-yl)aniline
  参考文献：
  名称：

  取代(1H-吡唑[3,4-b]吡啶)脲类化合物及其 抗肿瘤用途

  摘要：

  本发明提供了一种取代(1H‑吡唑[3,4‑b]吡啶)脲类化合物及其抗肿瘤用途。具体地，本发明提供了式I化合物及其药学上可接受的盐，其中，各基团的定义如说明书中所述。本发明的式I化合物可以抑制与肿瘤发生、发展相关的受体酪氨酸激酶(包括c‑Kit，PDGFRα和VEGFR2)，用于肿瘤的治疗。

  公开号：

  CN108117551B
• 作为产物：
  描述：

  对硝基苯甲醛 、 丙二酸环(亚)异丙酯 、 3-氨基-5-甲基吡唑 在 Fe+3(at)K₁₀ catalyst 作用下， 以 水 为溶剂， 反应 0.17h， 以93%的产率得到3-methyl-4-(4-nitrophenyl)-4,5-dihydro-1H-pyrazolo[3,4-b]pyridine-6(7H)-one
  参考文献：
  名称：

  一种绿色、高效、可回收的 Fe+3@K10 催化剂，用于在“水上”条件下合成具有生物活性的吡唑并[3,4-b]吡啶-6(7H)-酮

  摘要：

  摘要 4-芳基-3-甲基-4,5-二氢-1 H-吡唑并[3,4-b]吡啶-6(7 H )-酮及其双-酮的高效区域选择性一锅三组分合成描述了在 Sharpless 条件（“水上”条件）下由 Fe +3 -K10 蒙脱石（Fe +3 @K10）催化的衍生物（表 3 和图 2）。这种快速方法可以在很短的反应时间（10-15 分钟）和极好的收率（87-95%）内生成产物。检查合成产物的抗菌活性。一些产品显示出有希望的活性。

  DOI：

  10.1016/j.molstruc.2013.07.060

文献信息

• An efficient regioselective sonochemical synthesis of novel 4-aryl-3-methyl-4,5-dihydro-1H-pyrazolo[3,4-b]pyridin-6(7H)-ones
  作者：Abbas Azimi Roshan、Manouchehr Mamaghani、Nosrat Ollah Mahmoodi、Farhad Shirini

  DOI：10.1016/j.cclet.2011.12.009

  日期：2012.4

  An efficient ultrasound-assisted preparation of a series of novel 4-aryl-3-methyl-4,5-dihydro-1H-pyrazclo[3,4-b]pyridin-6(7H)ones via the reaction of 5-amino-3-methyl-1H-pyrazole, Meldrum's acid and various arylaldehydes using one-pot three-component approach is described. This rapid method produced the products in short reaction times (3-4 min) and excellent yields (87-95%). (C) 2011 Manouchehr Mamaghani. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
• Discovery of Potent, Selective Stem Cell Factor Receptor/Platelet Derived Growth Factor Receptor Alpha (c-KIT/PDGFRα) Dual Inhibitor for the Treatment of Imatinib-Resistant Gastrointestinal Stromal Tumors (GISTs)
  作者：Yanli Lu、Fei Mao、Xiaokang Li、Xinyu Zheng、Manjiong Wang、Qing Xu、Jin Zhu、Jian Li

  DOI：10.1021/acs.jmedchem.7b00468

  日期：2017.6.22

  Stem cell factor receptor (c-KIT) and platelet derived growth factor receptor alpha (PDGFR alpha) kinasts play an important role in gastrointestinal stromal tumors (GISTs). Here, we have discovered an c-KIT/PDGFR alpha dual inhibitor, compound 31, with single-digit nanomolar potency against c-KIT and PDGFRa. Compared to Imatinib (1), 31 showed better antiproliferative efficacy against various TEL-c-KIT/PD GFR alpha-BaF3 isogenic cells, including three 1-resistant BaF3 cell lines, as well as against GIST-T1 and GIST-882 cell lines. Furthermore, compound 31 showed a good KinomeScan selectivity (468 kinases) (S score (1) = 0.01 at 1 mu M concentration), good metabolic stability in liver microsomes, and no hERG inhibitory activity. It was worth noting that 31 inhibited GIST-T1 tumor growth (TGI = 81.5%) and even the BaF3-TEL-cKIT-T6701 tumor progression (TGI = 41.9%, 1-resistant GISTs) at a dosage of 100 mg/kg/day without exhibiting apparent toxicity.
• Heterocyclizations of 5-methylpyrazol-3-amine with unsaturated arylaliphatic carboxylic acid derivatives
  作者：V. V. Lipson、S. M. Desenko、M. G. Shirobokova、O. V. Shishkin、S. V. Shishkina

  DOI：10.1134/s1070428006070153

  日期：2006.7

  Cyclocondensation of 5-methylpyrazol-3-amine with methyl cinnamate and arylmethylidene-malonic acids in DMF and methanol leads to the formation of 7-aryl-2-methyl-6,7-dihydropyrazolo[1,5-a]pyrimidin-5(4H)-ones. Arylmethylidenemalonic acids react with the title amine at a ratio of 1: 2 in nitrobenzene to give 4-aryl-3,5-dimethyl-1,7-dihydrodipyrazolo[3,4-b:4',3'-e]pyridines. Heterocyclizations of 5-methylpyrazol-3-amine with 5-arylmethylidene-2,2-dimethyl-1,3-dioxane-4,6-diones or their precursors, para-substituted benzaldehydes and 2,2-dimethyl-1,3-dioxane-4,6-dione (Meldrum's acid) in all solvents (methanol, DMF, and nitrobenzene) give the corresponding 4-aryl-3-methyl-2,4,5,7-tetrahydropyrazolo[3,4-b]pyridin-6-ones. The structure of 3-methyl-4-(4-nitrophenyl)-2,4,5,7-tetrahydropyrazolo[3,4-b]pyridin-6-one was proved by X-ray analysis.
• A green, efficient and recyclable Fe+3@K10 catalyst for the synthesis of bioactive pyrazolo[3,4-b]pyridin-6(7H)-ones under "on water" conditions
  作者：Manouchehr Mamaghani、Farhad Shirini、Nosrat O. Mahmoodi、Abbas Azimi-Roshan、Hussein Hashemlou

  DOI：10.1016/j.molstruc.2013.07.060

  日期：2013.11

  Abstract An efficient regioselective one-pot three-component synthesis of 4-aryl-3-methyl-4,5-dihydro-1 H -pyrazolo[3,4-b]pyridin-6(7 H )-ones and their bis-derivatives ( Table 3 and Fig. 2 ) catalyzed by Fe +3 -K10 montmorillonite (Fe +3 @K10) under the Sharpless conditions (“On water” contdiions) is described. This rapid method produced the products in short reaction times (10–15 min) and excellent

  摘要 4-芳基-3-甲基-4,5-二氢-1 H-吡唑并[3,4-b]吡啶-6(7 H )-酮及其双-酮的高效区域选择性一锅三组分合成描述了在 Sharpless 条件（“水上”条件）下由 Fe +3 -K10 蒙脱石（Fe +3 @K10）催化的衍生物（表 3 和图 2）。这种快速方法可以在很短的反应时间（10-15 分钟）和极好的收率（87-95%）内生成产物。检查合成产物的抗菌活性。一些产品显示出有希望的活性。
• 取代(1H-吡唑[3,4-b]吡啶)脲类化合物及其 抗肿瘤用途
  申请人：华东理工大学

  公开号：CN108117551B

  公开（公告）日：2020-03-27

  本发明提供了一种取代(1H‑吡唑[3,4‑b]吡啶)脲类化合物及其抗肿瘤用途。具体地，本发明提供了式I化合物及其药学上可接受的盐，其中，各基团的定义如说明书中所述。本发明的式I化合物可以抑制与肿瘤发生、发展相关的受体酪氨酸激酶(包括c‑Kit，PDGFRα和VEGFR2)，用于肿瘤的治疗。