4,5-dihydronaphtho[1,2-d][1,2,3]selenadiazole | 59801-09-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4,5-dihydronaphtho[1,2-d][1,2,3]selenadiazole
• 英文别名: 4,5-dihydronaphto[1,2-d][1,2,3]selenadiazole；4,5-dihydro-naphtho[1,2-d][1,2,3]selenadiazole；4,5-Dihydronaphtho-<1,2-d><1,2,3>selenadiazol；4,5-Dihydrobenzo[e][1,2,3]benzoselenadiazole
• CAS: 59801-09-1
• 化学式: C₁₀H₈N₂Se
• 分子量: 235.147
• InChiKey: ZKWLDQHHFOPPST-UHFFFAOYSA-N

物化性质

• 沸点：
  363.7±40.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,5-dihydronaphtho[1,2-d][1,2,3]selenadiazole 在 氯磺酸 、 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 以39%的产率得到4,5-dihydro-3-selena-1,2-diaza-cyclopenta[a]naphthalene-8-sulfonic acid amide
  参考文献：
  名称：

  Synthesis and in vitro antifungal and cytotoxicity evaluation of substituted 4,5-dihydronaphtho[1,2-d][1,2,3]thia(or selena)diazoles

  摘要：

  Unsubstituted 4,5-dihydronaphtho[1,2-d][1,2,3]thia (or selena)diazoles (2a, 2b), prepared from the semicarbazone (1a), were nitrated using fuming nitric acid at 0 degrees C to yield various mono-nitrated dihydronaphthalenes (3a-3e). Related sulfamoyl derivatives (4a, 4b) were prepared using chlorosulfonic acid, followed by the addition of ammonia solution. Synthesis of 6,9-dimethoxy-4,5-dihydronaphtho[1,2-d][1,2,3]thiadiazole derivative (2c) was performed using 5,8-dimethoxy-alpha-tetralone semicarbazone (1b) and thionylchloride at low temperature. At 10 ppm concentration, all compounds showed low toxicity (higher than 80% survival) on brine shrimps, while at 100 ppm concentration compounds 2d, 3d, and 4b exhibited toxicity (less than 60% survival). Compounds 3a, 3e, and especially 4a showed significant antifungal activity against Cryptococcus neoformans. Compound 4a, while being the most active antifungal agent in this series, possessed low toxicity.

  DOI：

  10.1016/s0014-827x(02)00029-0
• 作为产物：
  描述：

  1-tetralone semicarbazone 在 selenium(IV) oxide 、 溶剂黄146 作用下， 反应 20.0h， 以34%的产率得到4,5-dihydronaphtho[1,2-d][1,2,3]selenadiazole
  参考文献：
  名称：

  4,5-二氢苯并二茂铁[1,2- d ] [1,2,3]硒代二唑及其苯并稠合类似物的合成，光谱和理论研究，X射线分析和抗增殖活性

  摘要：

  4,5-二氢萘[1,2- d ] [1,2,3]硒代二唑（1）和4,5-二氢苯并二茂铁[1,2- d ] [1，]的合成，结构测定及体外抗增殖作用2,3]硒代二唑（2）被提出。合成的分子通过NMR，IR，拉曼，质谱和UV光谱法表征。使用B3LYP / 6-31 + G *量子化学方法计算1和2的平衡结构，并通过单晶X射线衍射确定2的固相结构。1和2的抗增殖作用针对三种肿瘤性人类细胞系进行了研究。两种化合物都对宫颈HeLa和卵巢A2780细胞系具有活性，而2种化合物也对乳腺MDA-MB-231细胞生长具有活性。发现二茂铁衍生物2比其有机类似物1更有效。

  DOI：

  10.1016/j.jorganchem.2018.03.031

文献信息

• 신규한 셀레늄 고리 화합물 및 이의 제조방법
  申请人：KNU-Industry Cooperation Foundation 강원대학교산학협력단(220040088571) BRN ▼221-82-10213

  公开号：KR102037409B1

  公开（公告）日：2019-10-28

  2개 이상의 질소와 셀레늄이 고리 원소를 이루는 방향족 고리 화합물인 반응물질 1과, 적어도 이중 결합 이상의 결합을 갖는 반응물질 2를 로듐 촉매 반응 하에 반응시키는 단계; 및 상기 반응에 따라 상기 2개 이상의 질소위치에 상기 이중 결합 이상의 결합을 갖는 원소가 고리 원소로 첨가되어 셀레늄 고리 화합물이 합성되는 단계를 포함하며, 상기 반응물질 1 이고, 상기 반응물질 2는 알카인, 알켄, 나이트릴, 다이엔 결합 중 어느 하나를 포함하는 화합물인 것을 특징으로 하는 셀레늄 고리 화합물 합성 방법이 제공된다. (상기 R1, R2는 각각 수소, 할로겐기, 탄소수 1 내지 10의 알킬기, 탄소수 1 내지 10의 알케닐기, 탄소수 1 내지 10의 알키닐기, 탄소수 6 내지 12의 치환되거나 치환되지 않은 아릴기, 치환되거나 치환되지 않은 탄소수 5 내지 12의 헤테로아릴기 및 탄소수 1 내지 10의 알킬옥시로 이루어진 군으로부터 선택된 어느 하나이며, 상기 R1과 R2는 서로 연결되어 융합고리를 형성될 수 있음)

  2个以上的氮和硒形成环元素的芳香环化合物的反应物质1，至少具有双键以上的键合的反应物质2在铑催化反应下反应的步骤；以及根据所述反应，在所述2个以上的氮位置上，具有双键以上的键合的元素被添加为环元素以合成硒环化合物的步骤，其中所述反应物质1，并且所述反应物质2是包含碱金属，烯烃，腈，二烯键中的任何一种的化合物的硒环化合物合成方法，其特征在于提供。 （其中R1，R2分别为氢，卤素，1到10个碳原子的烷基，1到10个碳原子的烯基，1到10个碳原子的烷基，6到12个被取代或未被取代的芳基，5到12个被取代或未被取代的杂环芳基和1到10个烷氧基中的任何一个，其中R1和R2可以相互连接以形成融合环）
• Meier,H. et al., Chemische Berichte, 1976, vol. 109, p. 1650 - 1656
  作者：Meier,H. et al.

  DOI：——

  日期：——
• Synthesis, spectral- and theoretical study, x-ray analysis, and antiproliferative activity of 4,5-dihydrobenzoferroceno[1,2-d][1,2,3]selenadiazole and its benzo-fused analogue
  作者：Tibor Pasinszki、Dániel Dzsotján、Győző György Lajgut、Veronika Harmat、Andrea Bor、István Zupkó、Antal Csámpai

  DOI：10.1016/j.jorganchem.2018.03.031

  日期：2018.5

  was determined by single crystal X-ray diffraction. The antiproliferative effect of 1 and 2 was investigated against three tumorous human cell lines. Both compounds were active against cervical HeLa and ovarian A2780 cell lines, and 2 was also active against breast MDA-MB-231 cell growth. The ferrocene derivative 2 was found to be more effective than its organic analogue 1.

  4,5-二氢萘[1,2- d ] [1,2,3]硒代二唑（1）和4,5-二氢苯并二茂铁[1,2- d ] [1，]的合成，结构测定及体外抗增殖作用2,3]硒代二唑（2）被提出。合成的分子通过NMR，IR，拉曼，质谱和UV光谱法表征。使用B3LYP / 6-31 + G *量子化学方法计算1和2的平衡结构，并通过单晶X射线衍射确定2的固相结构。1和2的抗增殖作用针对三种肿瘤性人类细胞系进行了研究。两种化合物都对宫颈HeLa和卵巢A2780细胞系具有活性，而2种化合物也对乳腺MDA-MB-231细胞生长具有活性。发现二茂铁衍生物2比其有机类似物1更有效。
• Synthesis and in vitro antifungal and cytotoxicity evaluation of substituted 4,5-dihydronaphtho[1,2-d][1,2,3]thia(or selena)diazoles
  作者：A.R Jalilian、S Sattari、M Bineshmarvasti、M Daneshtalab、Abbas Shafiee

  DOI：10.1016/s0014-827x(02)00029-0

  日期：2003.1

  Unsubstituted 4,5-dihydronaphtho[1,2-d][1,2,3]thia (or selena)diazoles (2a, 2b), prepared from the semicarbazone (1a), were nitrated using fuming nitric acid at 0 degrees C to yield various mono-nitrated dihydronaphthalenes (3a-3e). Related sulfamoyl derivatives (4a, 4b) were prepared using chlorosulfonic acid, followed by the addition of ammonia solution. Synthesis of 6,9-dimethoxy-4,5-dihydronaphtho[1,2-d][1,2,3]thiadiazole derivative (2c) was performed using 5,8-dimethoxy-alpha-tetralone semicarbazone (1b) and thionylchloride at low temperature. At 10 ppm concentration, all compounds showed low toxicity (higher than 80% survival) on brine shrimps, while at 100 ppm concentration compounds 2d, 3d, and 4b exhibited toxicity (less than 60% survival). Compounds 3a, 3e, and especially 4a showed significant antifungal activity against Cryptococcus neoformans. Compound 4a, while being the most active antifungal agent in this series, possessed low toxicity.