3-(1H-四唑-5-基)-9H-噻吨-9-酮 10,10-二氧化物 | 51762-95-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻喃类
• 中文名称: 3-(1H-四唑-5-基)-9H-噻吨-9-酮 10,10-二氧化物
• 中文别名: 3-(1H-四唑-5-基)-9H-噻吨-9-酮10,10-二氧化物
• 英文名称: doxantrazole
• 英文别名: 10,10-dioxo-3-(1(2)H-tetrazol-5-yl)-10H-10λ⁶-thioxanthen-9-one；3-(1H-tetrazol-5-yl)-9H-thioxanthen-9-one 10,10-dioxide；3-(1H-tetrazol-5-yl)-9H-thio-xanthen-9-one 10,10-dioxide；3-(5-tetrazolyl)thioxanthone-10,10-dioxide；3-(5-Tetrazolyl)-thioxanthon-10,10-dioxid；10,10-dioxo-3-(2H-tetrazol-5-yl)thioxanthen-9-one
• CAS: 51762-95-9
• 化学式: C₁₄H₈N₄O₃S
• 分子量: 312.309
• InChiKey: VIDCTSLIEZMQRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  3-(1H-四唑-5-基)-9H-噻吨-9-酮 10,10-二氧化物 在 硫酸 作用下， 反应 1.5h， 生成 3-aminothioxanthen-9-one 10,10-dioxide
  参考文献：
  名称：

  Selective Inhibitors of Monoamine Oxidase. 2. Arylamide SAR

  摘要：

  Monoamine oxidase (MAO) exists in two forms distinguishable by substrate specificity. Inhibition of MAO A is believed to be responsible for the antidepressant activity of MAO inhibitors. A group of N-arylacetamides are highly specific inhibitors of MAO A, some with IC50 values in the 10-100 nM range. The requirements for high activity and specificity include a nearly linear tricyclic aromatic portion but a larger and a smaller central ring component. The amide group, which is best acetamido, is optimally placed para to the smaller central group. The size and shape of the aromatic moiety appear to be the major influence on activity and specificity for MAO A.

  DOI：

  10.1021/jm00039a021
• 作为产物：
  描述：

  2-benzenesulfonyl-4-(1(2)H-tetrazol-5-yl)-benzoic acid 在 水 、 溶剂黄146 作用下， 以 硫酸 为溶剂， 反应 5.0h， 以to give 3-(5-tetrazolyl)thioxanthone-10,10-dioxide的产率得到3-(1H-四唑-5-基)-9H-噻吨-9-酮 10,10-二氧化物
  参考文献：
  名称：

  Antiallergic cyclic sulphur compounds

  摘要：

  某些三环噻吲-10,10-二氧化物化合物，其中每个化合物在1-,2-,3-或4-位置上被羧基或(5-四唑基)基团取代，且每个化合物在5-,6-,7-或8-位置上可以被第二个羧基或(5-四唑基)基团或从氰基，卤素，硝基，烷基，烷氧基，酰基，氨基，酰胺基，硫代烷基，烷基磺酰氧基和烷基磺酰基中选择的取代基所取代，以及上述羧基取代化合物的可选取代酯和酰胺以及四唑基取代化合物的烷基衍生物，可用于缓解或预防过敏症状。

  公开号：

  US04103015A1

文献信息

• Cyclic sulphur compounds
  申请人：Burroughs Wellcome Co.

  公开号：US04012499A1

  公开（公告）日：1977-03-15

  Certain tricyclic thioxanthone-10,10-dioxide compounds each of which is substituted in the 1-,2-,3- or 4-position by a carboxyl or (5-tetrazolyl) group and each of which is optionally substituted in the 5-,6-,7- or 8-position by a second carboxyl or (5-tetrazolyl) group or a substituent selected from cyano, halogen, nitro, alkyl, alkoxy, acyl, amino, acylamino, thioalkyl, alkylsulphinyl and alkylsulphonyl, as well as salts, and optionally substituted esters and amides of the carboxyl substituted compounds and alkyl derivatives of the tetrazolyl substituted compounds, are useful for the relief or prophylaxis of allergic conditions.

  一些三环噻二氧杂蒽-10,10-二氧化物化合物，其中每个在1、2、3或4位被羧基或(5-四唑基)基取代，同时每个在5、6、7或8位可选择地被第二个羧基或(5-四唑基)基或氰基、卤素、硝基、烷基、烷氧基、酰基、氨基、酰胺基、硫代烷基、烷基砜基和烷基砜基等取代基取代，以及这些羧基取代化合物的盐、可选择地取代的酯和酰胺以及四唑基取代化合物的烷基衍生物，可用于缓解或预防过敏症状。
• Preparation of prodrugs for selective drug delivery
  申请人：Mills L. Randell

  公开号：US20050080260A1

  公开（公告）日：2005-04-14

  Synthesis of a chemical compound having the formula A-B-C that may serve for applications such as drug delivery where A is a chemiluminescent, moiety, B is a photochromic moiety, and C is a biologically active moiety where A-B-C may serve as a prodrug. Novel synthetic methods of the present invention to form the prodrug comprised the steps of (1) forming a benzophenone, (2) forming a diaryl ethylene, (3) attaching a phthalimide moiety to at least one of the aryl groups of the ethylene to form a phthalimide-ethylene conjugate, (4) condensing two ethylene-phthalimide conjugates to form a phthalimide-pentadiene conjugate, (5) converting the phthalimide to the phthalhydrazide by reaction with hydrazine to form a carrier compound according to the present invention, and (6) reacting the carrier compound with an nucleophilic moiety of the drug to form the corresponding prodrug. Alternatively the carrier can be prepared by using the halo-substituted diaryl ethylene to make the corresponding cationic leuco dye-like compound with known methods. The cationic compound then is protected by reacting with a nucleophile and coupled with the aminophathalimide by palladium-catalyzed amination to form the protected phthalimide-pentadiene conjugate. The latter is refluxed with hydrazine to convert its phthalimide to the phthalhydrazide and acidified to give the carrier. An additional aspect of the present invention relates to the use of these compounds as antiviral agents for the treatment of viral infections such as HIV and as anticancer agents for the treatment of cancers such as bowel, lung, and breast cancer.

  合成具有A-B-C化学式的化合物，可用于药物传递等应用，其中A是化学发光基团，B是光致变色基团，C是生物活性基团，其中A-B-C可作为前药。本发明的新型合成方法用于形成前药，包括以下步骤：(1)形成苯酮，(2)形成二芳基乙烯，(3)将邻苯二甲酰亚胺基团连接到乙烯的至少一个芳基上，形成邻苯二甲酰亚胺-乙烯共轭物，(4)缩合两个乙烯-邻苯二甲酰亚胺共轭物，形成邻苯二甲酰亚胺-戊二烯共轭物，(5)通过与肼反应将邻苯二甲酰亚胺转化为邻苯二酰肼，形成本发明的载体化合物，(6)将载体化合物与药物的亲核基团反应，形成相应的前药。另外，可以通过使用卤代二芳基乙烯制备相应的阳离子类似的类似类似染料化合物。然后，通过与亲核试剂反应保护阳离子类似化合物，并通过钯催化的胺化与氨基邻苯二甲酰亚胺偶联，形成保护的邻苯二甲酰亚胺-戊二烯共轭物。后者与肼回流，将其邻苯二甲酰亚胺转化为邻苯二酰肼，并酸化以得到载体。本发明的另一个方面涉及将这些化合物用作抗病毒剂，用于治疗病毒感染，如HIV，以及用作抗癌剂，用于治疗结肠癌、肺癌和乳腺癌等癌症。
• Cyclic sulphur compounds triazolyl substituted phenoxathin 10, 10
  申请人：Burroughs Wellcome Co.

  公开号：US04145350A1

  公开（公告）日：1979-03-20

  Certain tricyclic sulphone compounds each of which is substituted in the 1-, 2-, 3- or 4-position by a carboxyl or (5-tetrazolyl) group and each of which is optionally substituted in the 5-, 6-, 7- or 8-position by a second carboxyl or (5-tetrazolyl) group or a substituent selected from cyano, halogen, nitro, alkyl, alkoxy, acyl, amino, acylamino, thioalkyl, alkylsulphinyl and alkylsulphonyl, as well as salts, and optionally substituted esters and amides of the carboxyl substituted compounds and alkyl derivatives of the tetrazolyl substituted compounds, are useful for the relief or prophylaxis of allergic conditions.

  某些三环磺酰化合物，其中每个化合物在1-、2-、3-或4-位被羧酸或（5-四唑基）基替代，且每个化合物在5-、6-、7-或8-位可选择被第二个羧酸或（5-四唑基）基或从氰基、卤素、硝基、烷基、烷氧基、酰基、氨基、酰胺基、硫代烷基、烷基磺酰基和烷基磺酰基中选择的取代基替代，以及羧酸取代化合物和四唑基取代化合物的烷基衍生物的盐，可选择的酯和酰胺，对于缓解或预防过敏症状是有用的。
• METHODS AND COMPOSITIONS FOR TREATING AMYLOID-RELATED DISEASES
  申请人：Kong Xianqi

  公开号：US20100113591A1

  公开（公告）日：2010-05-06

  Methods, compounds, pharmaceutical compositions and kits are described for treating or preventing amyloid-related disease.

  本发明涉及用于治疗或预防淀粉样蛋白相关疾病的方法、化合物、制药组合物和试剂盒。
• Tricyclic compounds, preparation, use and intermediates
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP0093381A1

  公开（公告）日：1983-11-09

  Tricyclic compounds of formula (I) wherein X' is a carboxyl or 5-tetrazolyl group X2 is carbonyl or methylene X3 is hydroxyl or a group -X4(CnH2n)X5 where X4 is oxygen or sulphur X6 is hydrogen or a group -OX6 where X6 is hydrogen, alkanoyl of 1 to 4 carbon atoms or a group -(CmH2m)X7 where X7 is hydrogen or a group -OX8 where X8 is hydrogen or alkanoyl of 1 to 4 carbon atoms and m and n are each, independently, an integer from 1 to 4, together with salts thereof, provided that when X5 is a group -OX6 then n is always greater than 1 and X4 and X5 are attached to different carbon atoms and that when X7 is a group -OX8 then m is always greater than 1 and no single carbon atom in the radical -(CmH2m)-is attached to two oxygen atoms. These compounds are of value in medicine in circumstances where it is desirable to provide a more effective delivery of oxygen to the tissues; in vivo applications include the relief or amelioration of tissue hypoxia as in, for example, cardiac or cerebral ischaemia while in vitro they maintain the oxygen-delivery capacity of stored red blood cells and prolong the cells' useful storage life. The invention is also directed to methods for the preparation of the compounds, to pharmaceutical formulations and other presentation forms containing them and the preparation thereof, to the use of the compounds in medicine, and to novel intermediates for the said compounds and the preparation thereof.

  式 (I) 的三环化合物 其中 X' 是羧基或 5-四唑基 X2 是羰基或亚甲基 X3 是羟基或基团 -X4(CnH2n)X5 其中 X4 是氧或硫 X6 是氢或基团 -OX6 其中 X6 是氢、1 至 4 个碳原子的烷酰基或基团-(CmH2m)X7 其中 X7 是氢或基团 -OX8 其中 X8 是氢或 1 至 4 个碳原子的烷酰基，m 和 n 各自独立地为 1 至 4 的整数，以及它们的盐、 条件是当 X5 为基团-OX6 时，n 始终大于 1，且 X4 和 X5 连接在不同的碳原子上 当 X7 为基团-OX8 时，m 始终大于 1，且自由基-(CmH2m)-中没有单个碳原子与两个氧原子相连。 这些化合物在医学上的应用价值在于，可以更有效地向组织输送氧气；在体内的应用包括缓解或改善组织缺氧，如心肌或脑缺血，而在体外的应用则是保持储存的红细胞的氧气输送能力，延长细胞的有效储存寿命。 本发明还涉及这些化合物的制备方法、含有这些化合物的药物制剂和其他呈现形式及其制备方法、这些化合物在医学中的用途，以及上述化合物的新型中间体及其制备方法。