3-amino-4-imino-4H-thieno<3,4-c><1>benzopyran | 41078-19-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3-amino-4-imino-4H-thieno<3,4-c><1>benzopyran
• 英文别名: 3-Imino-3H-thieno[3,4-c][1]benzopyran-4-amine；4-iminothieno[3,4-c]chromen-3-amine
• CAS: 41078-19-7
• 化学式: C₁₁H₈N₂OS
• 分子量: 216.263
• InChiKey: KCQQIJXAAAVVQY-UHFFFAOYSA-N

物化性质

• 熔点：
  158-160 °C(Solv: xylene (1330-20-7))
• 沸点：
  427.2±55.0 °C(Predicted)
• 密度：
  1.55±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  87.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-amino-4-imino-4H-thieno<3,4-c><1>benzopyran 以33%的产率得到
  参考文献：
  名称：

  NyiondiBonguen E., Sopbue Fondjo E., Fomum Tanee, Doepp Dietrich, J. Chem. Soc. Perkin Trans. 1, (1994) N 15, S 2191- 2195

  摘要：

  DOI：
• 作为产物：
  描述：

  2-Imino-3-methyl-2H-1-benzopyran-3-carbonitrile 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 氨 作用下， 以 乙醇 为溶剂， 生成 3-amino-4-imino-4H-thieno<3,4-c><1>benzopyran
  参考文献：
  名称：

  Synthesis, characterization, antimicrobial activities and electrochemical behavior of new phenolic azo dyes from two thienocoumarin amines

  摘要：

  The coupling reactions of diazotized thienocoumarin derivatives with p-acetaminophen, salicylic acid and acetylsalicylic acid gave four products in which the benzene ring of the phenolic reagents were primarily substituted by two 3-diazenyl-4H-thieno[3,4-c]chromen-4-one or 3-diazenyl-4-imino-4H-thieno[3,4-c]chromene moieties. The newly prepared azo dyes were fully characterized based on their analytical and spectroscopic data. The electrochemical analysis of the novel azo dyes carried out on a glassy carbon electrode unequivocally further confirmed the assigned structures. The synthesized compounds tested for their antimicrobial activity using broth microdilution method, showed good activities.[GRAPHICS].

  DOI：

  10.24820/ark.5550190.p010.994

文献信息

• Evaluation of macrofilaricidal and microfilaricidal activities against Onchocerca ochengi and cytotoxicity of some synthesized azo compounds containing thiophene backbone
  作者：Joseph Tsemeugne、Lahngong M. Shinyuy、Sorel K. D. Djeukoua、Emmanuel F. Sopbue、Moses N. Ngemenya

  DOI：10.1007/s00436-021-07162-3

  日期：2021.6

  MTT formazan assay. Cytotoxicity of active compounds was assessed on monkey kidney epithelial cells (LLC-MK2) using the MTT formazan assay. Seven (7) compounds showed both macrofilaricidal activity against adult male worms and microfilaricidal activity among which three 4a, 4c and 4e recorded the highest activity (IC50 = 4.2 to 8.8μM) against adult male worms, comparable to some standard anthelmintics

  盘尾丝虫病（一种由盘尾丝虫（Onchocerca volvulus）引起的毁灭性热带丝虫病）的控制和治疗完全依赖于伊维菌素的社区指导治疗。但是，伊维菌素仅具有微杀丝作用，除其他局限性外还具有寄生虫抵抗力的证据，因此有必要寻找新的有效和安全的杀纤维剂。根据蠕虫的蠕动和MTT formazan分析，在体外筛选了十种合成的噻吩基氮唑基染料，以对抗Onchocerca ochengi的成虫和微丝虫蠕虫阶段。使用MTT甲maz试验评估活性化合物对猴肾上皮细胞（LLC-MK2）的细胞毒性。七（7）种化合物同时显示了对成年雄性蠕虫的大杀线活性和微杀线活性，其中三个图4a，4c和4e记录了对成年雄性蠕虫的最高活性（IC 50 = 4.2至8.8μM），与某些标准驱虫药相当。孵育24小时后，五种化合物显示出对微丝虫病的快速活性，并具有100％的抑制作用。活性化合物对猴肾细胞无毒（CC 50 >4μg/ mL
• Reactions of some anellated 2-aminothiophenes with electron poor acetylenes
  作者：Emmanuel Sopbué Fondjo、Dietrich Döpp、Gerald Henkel

  DOI：10.1016/j.tet.2006.04.037

  日期：2006.7

  saturated carbocycle and (b) [3,4-c]-anellation to benzopyrans, towards typical acetylenic dienophiles has been investigated. Because of the absence of conjugation, the thiophenes of type (a) do not undergo [4+2]-cycloaddition with acetylenic dienophiles. Instead, the N-vinylated products 2 and 3 were obtained with dimethyl acetylene dicarboxylate (DMAD). Electron poor alkynes react with the thiophenes of

  2-氨基噻吩在两个不同anellations的反应性：（1）[ b ] -anellation饱和碳环和（b）[3,4 Ç ] -anellation到苯并吡喃，向典型的炔属亲二烯体进行了研究。由于不存在共轭作用，（a）型噻吩不会与炔属二烯亲和物发生[4 + 2]-环加成反应。取而代之的是，用乙炔二甲酸二甲酯（DMAD）获得N-乙烯基化产物2和3。在[4 + 2] -mode在二恶烷，得到的产品DMAD发生反应：贫电子炔烃与式（b）中的在三种主要方式噻吩反应7，8和14; 迈克尔加成反应型也发生在双亚乙烯基同源个碳原子（C-1中的起始原料4，9和10）在二恶烷，甲醇或乙醇。丙酸甲酯以类似的方式反应。所述双重Ñ -vinylated产物26从获得的10在甲苯和C-1乙烯化产物24B和27，从而获得9的二恶烷和10在甲醇中。反应10用丙炔酸苯乙酯在二甲基甲酰胺中的溶液不产生加成产物，而是炔属试
• Coupling of two diazotized 3-aminothieno[3,4-c]coumarins with aromatic amines
  作者：Emmanuel Sopbué Fondjo、Joseph Tsemeugne、Beibam Luc Sondengam、Thomas Oppenlaender、Hippolyte Kamdem Wabo、Pierre Tane、Joseph D. Connolly、Wim Dehaen、Taoufik Rohand、Haruhisa Kikuchi、Yoshiteru Oshima

  DOI：10.1002/jhet.757

  日期：2011.11

  diazotized intermediates 2 and 3, the latter resulting from the acid ‐catalyzed hydrolysis of the lactonic ring of 2. The in situ formed diazonium salts react with aromatic amines (4) to afford a series of arylazothiophenes dyes in the form of their ammonium sulfate salts. With diazotized aniline, besides the normally expected phenylazothiophene 10 from the reaction with compound 1a, the corresponding product

  研究了两种重氮化的3-氨基噻吩并[3,4-c]香豆素的偶联反应。化合物1a，1b都与亚硝酸钠在0-5°C的浓硫酸中反应，得到重氮化的中间体2和3，后者是由酸催化的2的内酯环水解而成的。在原位形成的重氮盐与芳族胺（反应4）得到的一系列arylazothiophenes染料在它们的硫酸铵盐的形式。除了通常预期的与化合物1a反应产生的苯偶氮噻吩10外，还可以使用重氮化苯胺，还分离出相应的酸水解产物11。在至少一种情况下，噻吩重氮盐2与对硝基苯胺进行Gomberg-Bachmann芳基化反应，得到2-芳基噻吩9。化合物1a，1b被浓硫酸直接水解，随后酸水解的主要产物氧化二聚，生成化合物12。J.杂环化​​学。（2011）。
• Synthesis and antimicrobial activities of some novel thiophene containing azo compounds
  作者：Emmanuel Sopbué Fondjo、Joseph Tsemeugne、Jean De Dieu Tamokou、Arnaud Ngongang Djintchui、Jules Roger Kuiate、Beibam Luc Sondengam

  DOI：10.1515/hc-2013-0096

  日期：2013.8.1

  A series of new thienylazothiophenes were prepared by coupling reactions of diazotized thienocoumarins with their corresponding free amines. The structures of the products 3–7 were assigned on the basis of their elemental and spectroscopic data. The HMBC and HSQC techniques were used in some cases to ascertain the structural assignments. The antimicrobial screenings of compounds 3–7 along with substituted 2-aminothiophenes 1a,b were performed against three bacteria and three fungal species and their activities compared to those of nystatin, gentamycin and ciprofloxacin used as reference drugs. It was found that the antimicrobial activities of the tested new hybrid compounds were in some cases equal or better than those of the reference drugs.

  一系列新的噻吩基氮代噻吩被制备出来，通过将重氮化的噻吩香豆素与相应的游离胺偶联反应。根据元素和光谱数据，产品3-7的结构被确定。在某些情况下，使用HMBC和HSQC技术来确定结构分配。化合物3-7以及取代的2-氨基噻吩1a、1b与三种细菌和三种真菌进行抗菌筛选，并将它们的活性与作为参考药物的尼斯他汀、庆大霉素和环丙沙星进行比较。发现被测试的新混合化合物的抗菌活性在某些情况下等同或优于参考药物。
• Condensation reactions of 3-Amino-4-imino-4<i>H</i>-thieno-[3,4-<i>c</i>][1]benzopyran
  作者：E. Nyiondi-Bonguen、E. Sopbué Fondjo、Z. Tanee Fomum、Dietrich Döpp

  DOI：10.1002/jhet.5570330212

  日期：1996.3

  compound 1 reacts with trifluoroacetic anhydride to give the doubly trifluoracetylated derivative 2 and in addition the coumarin derivative 3. In refluxing DMF, two moles of 1 react with loss of one molecule of ammonia to afford 4, which undergoes subsequent N-acylation by β-dicarbonyl compounds 9a-f to yield N-acyl derivatives 10a-f. With dimethyl malonate (9a) besides compound 10a, the cycloacylated compound

  标题化合物1与三氟乙酸酐反应，得到双三氟乙酰化衍生物2，此外还产生香豆素衍生物3。在回流的DMF中，两摩尔的1与失去一分子的氨反应以得到4，其随后通过β-二羰基化合物9a-f进行N-酰化以产生N-酰基衍生物10a-f。除了化合物10a以外，通过丙二酸二甲酯（9a），也以良好的收率获得了环酰化的化合物11。化合物11容易被酸和碱水解和脱羧成前述的稠合衍生物12。后者可以通过碱水溶液的作用转化为新的噻吩并嘧啶酮衍生物。