6-chloro-3-nitro-N-propylpyridin-2-amine | 1044770-83-3

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 6-chloro-3-nitro-N-propylpyridin-2-amine
• CAS: 1044770-83-3
• 化学式: C₈H₁₀ClN₃O₂
• 分子量: 215.639
• InChiKey: YRVNROHEUWUGQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  70.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-chloro-3-nitro-N-propylpyridin-2-amine 在 sodium dithionite 、 potassium carbonate 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 反应 5.0h， 生成 2-(1H-indol-3-yl)-5-(4-methylpiperazin-1-yl)-3-propyl-3H-imidazo[4,5-b]pyridine
  参考文献：
  名称：

  Synthesis and Anti-inflammatory Evaluation of Novel Benzimidazole and Imidazopyridine Derivatives

  摘要：

  Sepsis, an acute inflammatory disease, remains the most common cause of death in intensive care units. A series of benzimidazole and imidazopyridine derivatives were synthesized and screened for anti-inflammatory activities, and the imidazopyridine series showed excellent inhibition of the expression of inflammatory cytokines in LPS-stimulated macrophages. Compounds X10, X12, X13, X14, and X15 inhibited TNF-alpha and IL-6 release in a dose-dependent manner, and X12 showed no cytotoxicity in hepatic cells. Furthermore, X12 exhibited a significant protection against LPS-induced septic death in mouse models. Together, these data present a series of new imidazopyridines with potential therapeutic effects in acute inflammatory diseases.

  DOI：

  10.1021/ml300282t
• 作为产物：
  描述：

  正丙胺 、 2,6-二氯-3-硝基吡啶 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 6-chloro-3-nitro-N-propylpyridin-2-amine
  参考文献：
  名称：

  Synthesis and Anti-inflammatory Evaluation of Novel Benzimidazole and Imidazopyridine Derivatives

  摘要：

  Sepsis, an acute inflammatory disease, remains the most common cause of death in intensive care units. A series of benzimidazole and imidazopyridine derivatives were synthesized and screened for anti-inflammatory activities, and the imidazopyridine series showed excellent inhibition of the expression of inflammatory cytokines in LPS-stimulated macrophages. Compounds X10, X12, X13, X14, and X15 inhibited TNF-alpha and IL-6 release in a dose-dependent manner, and X12 showed no cytotoxicity in hepatic cells. Furthermore, X12 exhibited a significant protection against LPS-induced septic death in mouse models. Together, these data present a series of new imidazopyridines with potential therapeutic effects in acute inflammatory diseases.

  DOI：

  10.1021/ml300282t

文献信息

• WO2024067465A1
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis and Insecticidal Activity of Novel Nitropyridyl-Based Dichloropropene Ethers
  作者：Aiping Liu、Wanqi Yu、Minhua Liu、Jianjun Bai、Weidong Liu、Xingping Liu、Hui Pei、Li Hu、Mingzhi Huang、Xiaoguang Wang

  DOI：10.1021/acs.jafc.5b02279

  日期：2015.9.2

  Dihalopropene ether insecticides are known for good features such as no cross-resistance to other insecticide classes and safety for mammals. Pyridalyl is the only currently commercialized dichloropropene ether insecticide; however, it contains a trifluoromethyl group, the synthesis of which requires harsh reagents and reaction conditions. To search for novel dihalopropene ethers with unique biological activities but without trifluoromethyl groups, a series of nitropyridyl-based dichloropropene ether analogues were synthesized by reacting nitro-based halopyridine with 2,6-dichloro-4-(3,3-dichloroallyloxy)phenol or 2,6-dichloro-4-(3,3-dichloroallyloxy)phenyl 3-hydroxypropyl ether. Bioassay showed that the compounds exhibited potent insecticidal activities against various lepidopteran pests. Particularly, 2,6-dichloro-4-(3,3-dichloroallyloxy)phenyl 3-(5-nitro-2-pyridyloxy)propyl ether (8e) was active against major agricultural pests, and its insecticidal potency was comparable to that of Pyridalyl. Besides the trifluoromethyl group in Pyridalyl, a nitro group on the 5-position of the pyridyl ring is also viable for the development of optimal insecticidal activity.
• Synthesis and Anti-inflammatory Evaluation of Novel Benzimidazole and Imidazopyridine Derivatives
  作者：Gaozhi Chen、Zhiguo Liu、Yali Zhang、Xiaoou Shan、Lili Jiang、Yunjie Zhao、Wenfei He、Zhiguo Feng、Shulin Yang、Guang Liang

  DOI：10.1021/ml300282t

  日期：2013.1.10

  Sepsis, an acute inflammatory disease, remains the most common cause of death in intensive care units. A series of benzimidazole and imidazopyridine derivatives were synthesized and screened for anti-inflammatory activities, and the imidazopyridine series showed excellent inhibition of the expression of inflammatory cytokines in LPS-stimulated macrophages. Compounds X10, X12, X13, X14, and X15 inhibited TNF-alpha and IL-6 release in a dose-dependent manner, and X12 showed no cytotoxicity in hepatic cells. Furthermore, X12 exhibited a significant protection against LPS-induced septic death in mouse models. Together, these data present a series of new imidazopyridines with potential therapeutic effects in acute inflammatory diseases.