3-氨基-6-(噻吩-3-基)吡嗪 | 105538-02-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 3-氨基-6-(噻吩-3-基)吡嗪
• 英文名称: 3-amino-6-(thiophen-3-yl)pyridazine
• 英文别名: 3-amino-6-(3-thienyl)pyridazine；6-(thien-3-yl)pyridazin-3-amine；3-amino-6-thienylpyridazine；6-(Thiophen-3-yl)pyridazin-3-amine；6-thiophen-3-ylpyridazin-3-amine
• CAS: 105538-02-1
• 化学式: C₈H₇N₃S
• 分子量: 177.23
• InChiKey: ZVCNZVHKKQNZRF-UHFFFAOYSA-N

物化性质

• 沸点：
  373.2±27.0 °C(Predicted)
• 密度：
  1.333±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  3-氨基-6-(噻吩-3-基)吡嗪 在 N-碘代丁二酰亚胺 作用下， 以 乙二醇二甲醚 、 乙腈 为溶剂， 反应 3.0h， 生成 3-iodo-2-tert-butyl-6-(thien-3-yl)imidazo[1,2-b]pyridazine
  参考文献：
  名称：

  3-联苯基咪唑并[1,2- a ]吡啶或[1,2- b ]哒嗪及其类似物，新型黄病毒科抑制剂

  摘要：

  以Ttou 84为起点，设计了一类新型的咪唑并[1,2- a ]吡啶和咪唑并[1,2- b ]哒嗪联苯衍生物，以优化其对牛病毒性腹泻病毒复制的抑制作用（ BVDV）和丙型肝炎病毒（HCV）。选择药物调节的三个位点，即中央杂环核心结构上的位置2、3和6。在测试的49个类似物中，只有化合物18j（3-（2'-hydroxybiphen-3-yl）-2-（2-甲氧基苯基）-6-（thien-3-yl）咪唑并[1,2- b ]哒嗪在HCV复制子系统中显示抗病毒活性，使人联想到选择性抑制（抑制60-70％）。化合物4f（3-（联苯-3-基）-2-（4-氟苯基）-6-苯硫基咪唑并[1,2- a吡啶]被证明是BVDV复制的最有选择性的抑制剂，与瘟病毒复制的已知抑制剂没有或仅有很小的交叉耐药性。4f的交叉电阻谱可能表明4f与BPIP，VP32947，AG110或LZ37没有与相同的结合位点相互作用。从针对

  DOI：

  10.1016/j.ejmech.2013.03.054
• 作为产物：
  描述：

  6-(3-thienyl)pyridazin-3(2H)-one 在 镍 氢气 、 一水合肼 、 三氯氧磷 作用下， 以 甲醇 、 正丁醇 为溶剂， 20.0~100.0 ℃ 、101.33 kPa 条件下， 反应 10.0h， 生成 3-氨基-6-(噻吩-3-基)吡嗪
  参考文献：
  名称：

  一系列作为选择性GABA-A拮抗剂的γ-氨基丁酸氨基哒嗪衍生物的合成与构效关系。

  摘要：

  我们最近发现，GABA的芳基氨基哒嗪衍生物SR 95103 [2-（3-羧丙基）-3-氨基-4-甲基-6-苯基吡啶并鎓氯化物]是一种选择性和竞争性的GABA-A受体拮抗剂。为了进一步探索对GABA受体亲和力的结构要求，我们通过将各种哒嗪结构连接到GABA或GABA样侧链上，合成了38种化合物。大多数化合物从大鼠脑膜中取代了[3H] GABA。所有活性化合物都拮抗了GABA引起的[3H]地西p结合的增强，强烈表明所有这些化合物都是GABA-A受体拮抗剂。从大鼠脑膜置换[3H] GABA的化合物均未与其他GABA识别位点（GABA-B受体，GABA吸收结合位点，谷氨酸脱羧酶，GABA转氨酶）相互作用。它们不与与GABA-A受体相关的Cl-离子载体相互作用，也不与苯并二氮杂str，士的宁和谷氨酸结合位点相互作用。因此，这些化合物似乎是特异性的GABA-A受体拮抗剂。就结构活性而言，可以得出结论，

  DOI：

  10.1021/jm00385a003

文献信息

• A New Approach Towards the Synthesis of 3-Amino-6-(hetero)arylpyridazines Based on Palladium Catalyzed Cross-coupling Reactions
  作者：Bert U.W Maes、Guy L.F Lemière、Roger Dommisse、Koen Augustyns、Achiel Haemers

  DOI：10.1016/s0040-4020(00)00083-1

  日期：2000.3

  The synthesis of 3-amino-6-(hetero)arylpyridazines via palladium catalyzed cross-coupling reactions (Suzuki, Stille) on 3-amino-6-chloropyridazine (1a) and 3-amino-6-iodopyridazine (1b) has been investigated. Comparison of the results shows that there is no need to start from 1b. An improved method for the synthesis of compound 1b from 1a is also described.

  经由钯的3-氨基-6-（杂）arylpyridazines合成上的3-氨基-6-氯哒嗪（催化的交叉偶联反应（铃木，的Stille）1A）和3-氨基-6- iodopyridazine（1B）进行了研究。结果比较表明，无需从1b开始。还描述了一种由1a合成化合物1b的改进方法。
• [EN] INHIBITORS OF ANOCTAMIN 6 PROTEIN AND USES THEREOF<br/>[FR] INHIBITEURS DE LA PROTÉINE ANOCTAMINE 6 ET LEURS UTILISATIONS
  申请人：ILDONG PHARMACEUTICAL CO LTD

  公开号：WO2022157686A1

  公开（公告）日：2022-07-28

  The present invention relates to a new compound that can inhibit an anoctamin 6 protein, a composition comprising the compound, a method for preparing the compound, and a method for using the compound or composition.

  本发明涉及一种新化合物，可以抑制anoctamin 6蛋白质，包括该化合物的组合物，制备该化合物的方法，以及使用该化合物或组合物的方法。
• Mild and Direct Access to 7-Substituted-4-trifluoromethylpyrimido[1,2-b]pyridazin-2-one Systems
  作者：Mohamed Abarbri、Julien Petrignet、Emilie Thiery、Laurence Silpa

  DOI：10.1055/s-0033-1340664

  日期：——

  New and efficient methods for the synthesis of 7-substituted-4-trifluoromethylpyrimido[1,2-b]pyridazin-2-one derivatives using either two-step Suzuki/heterocyclization, or two-step heterocyclization/substitution sequences are developed. A variety of substituted products are obtained in good to excellent yields from 3-amino-6-chloropyridazine and ethyl 4,4,4-trifluorobut-2-ynoate.
• Competitive antagonism of insect GABA receptors by iminopyridazine derivatives of GABA
  作者：Mohammad Mostafizur Rahman、Yuki Akiyoshi、Shogo Furutani、Kazuhiko Matsuda、Kenjiro Furuta、Izumi Ikeda、Yoshihisa Ozoe

  DOI：10.1016/j.bmc.2012.07.049

  日期：2012.10

  A series of 4-(6-imino-3-aryl/heteroarylpyridazin-1-yl) butanoic acids were synthesized and examined for antagonism of GABA receptors from three insect species. When tested against small brown planthopper GABA receptors, the 3,4-methylenedioxyphenyl and the 2-naphthyl analogues showed complete inhibition of GABA-induced fluorescence changes at 100 mu M in assays using a membrane potential probe. Against common cutworm GABA receptors, these analogues displayed approximately 86% and complete inhibition of GABA-induced fluorescence changes at 100 mu M, respectively. The 4-biphenyl and 4-phenoxyphenyl analogues showed moderate inhibition at 10 mu M in these receptors, although the inhibition at 100 mu M was not complete. Against American cockroach GABA receptors, the 4-biphenyl analogue exhibited the greatest inhibition (approximately 92%) of GABA-induced currents, when tested at 500 mu M using a patch-clamp technique. The second most active analogue was the 2-naphthyl analogue with approximately 85% inhibition. The 3-thienyl analogue demonstrated competitive inhibition of cockroach GABA receptors. Homology modeling and ligand docking studies predicted that hydrophobic 3-substituents could interact with an accessory binding site at the orthosteric binding site. (C) 2012 Elsevier Ltd. All rights reserved.
• A small-molecule cell-based screen led to the identification of biphenylimidazoazines with highly potent and broad-spectrum anti-apicomplexan activity
  作者：Espérance Moine、Caroline Denevault-Sabourin、Françoise Debierre-Grockiego、Laurence Silpa、Olivier Gorgette、Jean-Christophe Barale、Philippe Jacquiet、Fabien Brossier、Alain Gueiffier、Isabelle Dimier-Poisson、Cécile Enguehard-Gueiffier

  DOI：10.1016/j.ejmech.2014.10.057

  日期：2015.1

  An in vitro screening of the anti-apicomplexan activity of 51 compounds, stemming from our chemical library and from chemical synthesis, was performed. As a study model, we used Toxoplasma gondii (T. gondii), expressing beta-galactosidase for the colorimetric assessment of drug activity on parasites cultivated in vitro. This approach allowed the validation of a new series of molecules with a biphenylimidazoazine scaffold as inhibitors of T. gondii growth in vitro. Hence, 8 molecules significantly inhibited intracellular replication of T. gondii in vitro, with EC50 < 1 mu M, while being non-toxic for human fibroblasts at these concentrations. Most attractive candidates were then selected for further biological investigations on other apicomplexan parasites (Neospora caninum, Besnoitia besnoiti, Eimeria tenella and Plasmodium falciparum). Finally, two compounds were able to inhibit growth of four different apicomplexans with EC50 in the submicromolar to nanomolar range, for each parasite. These data, including the broad anti-parasite spectrum of these inhibitors, define a new generation of potential anti-parasite compounds of wide interest, including for veterinary application. Studies realized on E. tenella suggest that these molecules act during the intracellular development steps of the parasite. Further experiments should be done to identify the molecular target(s) of these compounds. (C) 2014 Elsevier Masson SAS. All rights reserved.