1,2-dihydrobenzotriazol-4-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: 1,2-dihydrobenzotriazol-4-one
• 化学式: C₆H₅N₃O
• 分子量: 135.12
• InChiKey: NPZTUJOABDZTLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  53.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  trans-2-phenylcyclopentan-1-ol 、 1,2-dihydrobenzotriazol-4-one 在 四丁基高氯酸铵 、 对甲苯磺酸 作用下， 以 乙腈 为溶剂， 以28 %的产率得到1-(6-phenyltetrahydro-2H-pyran-2-yl)-1,2-dihydro-4H-benzo[d][1,2,3]triazol-4-one
  参考文献：
  名称：

  无应变环烷醇的电化学解构和扩环官能化

  摘要：

  报道了一种从烷醇合成环醚和无环醛的有效且可持续的电化学方法。该策略已成功应用于具有不同环尺寸和不同类型亲核试剂的环烷醇。此外，机理研究表明反应经历连续过程，包括阳极氧化、β-断裂和亲核加成。该方法为从环烷醇和亲核试剂构建环醚和末端醛提供了一种新的合成方法。

  DOI：

  10.1021/acs.orglett.4c01337

文献信息

• Isoquinolinone-, phthalazinone-, quinazolinone- and benzotriazolinone derivatives, their preparation and their use as anti-thrombotics
  申请人：LUITPOLD PHARMA GmbH

  公开号：EP0649839A1

  公开（公告）日：1995-04-26

  The invention relates to heterocyclic carbamates of the formula (I) in which a) X denotes the group CR⁴ and Y denotes the group CR⁵, where R¹ stands for a C₁- to C₆- lower alkyl radical, for a substituted C₁- to C₆- lower alkyl radical, for an aryl-C₁- to C₆- lower alkyl radical, for an aryl radical or for a heterocyclic radical, R² and R³ independently of one another stand for radicals of the following meaning: hydrogen atoms, C₁- to C₆- lower alkyl radicals, C₁- to C₆- lower alkoxy radicals, C₁- to C₆- lower alkylthio radicals, halogen atoms, nitro groups, hydroxyl groups, trifluoromethyl radicals, cyano radicals, sulpho radicals, C₁- to C₆- lower alkylsulphonyl groups, carboxylic acid groups, C₁- to C₆- lower alkoxycarbonyl radicals, C₁- to C₆- lower alkoxycarbonyloxy radicals, acetamido radicals, benzamido radicals or the group -N(R⁶)R⁷, R⁴ and R⁵ independently of one another stand for a hydrogen atom, for a C₁- to C₆- lower alkyl radical, for a substituted C₁- to C₆- lower alkyl radical, for an aryl-C₁- to C₆- lower alkyl radical or for an aryl radical, m and n independently of one another are equal to 0, 1, 2, 3 or 4, and R⁶ and R⁷ independently of one another stand for a hydrogen atom or a C₁- to C₆- lower alkyl radical, or in which b) X and Y denote a nitrogen atom, where m, n, R¹, R², R³, R⁶ and R⁷ have the meanings mentioned under a), with the proviso that R¹ is not ethyl and if R¹ denotes a methyl radical, an unsubstituted C₃- to C₆- lower alkyl radical, a phenyl radical or a benzyl radical, at least one radical R² or R³ is different from a hydrogen atom or a halogen atom, or in which c) X denotes a nitrogen atom and Y denotes the radical CR⁵, where R¹ stands for a substituted C₁- to C₆- lower alkyl radical, for an aryl-C₁- to C₆- lower alkyl radical, for an aryl radical or for a heterocyclic radical, R⁵ stands for a hydrogen atom or for a C₁- to C₆- lower alkyl radical, and m, n, R², R³, R⁶ and R⁷ have the meanings mentioned under a), or in which d) X denotes a nitrogen atom and Y denotes the radical CR⁵, where R⁵ stands for a substituted C₁- to C₆- lower alkyl radical, for an aryl-C₁- to C₆- lower alkyl radical or for an aryl radical, and m, n, R¹, R², R³, R⁶ and R⁷ have the meanings mentioned under a), or in which e) Y denotes a nitrogen atom and X denotes the radical CR⁴, where R⁴ stands for a substituted C₁- to C₆- lower alkyl radical or for a radical of the general formula (II)         ―Z―R⁸   (II) where Z stands for a carbonyl or carboxyl group, a sulphur atom or an oxygen atom and R⁸ stands for a C₁- to C₆- lower alkyl radical, for a substituted C₁- to C₆- lower alkyl radical, for an aryl-C₁- to C₆- lower alkyl radical or for an aryl radical, and m, n, R¹, R², R³, R⁶ and R⁷ have the meanings mentioned under a), or in which f) Y denotes a nitrogen atom and X denotes the radical CR⁴, where R¹ stands for a substituted C₁- to C₆- lower alkyl radical, for an aryl radical or for a heterocyclic radical, R⁴ stands for a hydrogen atom, for a C₁- to C₆- lower alkyl radical, for a substituted C₁- to C₆- lower alkyl radical, for a substituted C₁- to C₆- lower alkyl radical, for an aryl-C₁- to C₆- lower alkyl radical or for an aryl radical, and m, n, R², R³, R⁶ and R⁷ have the meanings mentioned under a), with the proviso that if R², R³ and R⁴ denote hydrogen atoms, R¹ is different from an unsubsituted phenyl radical, and their salts with physiologically tolerable acids and bases, and their use as antithrombotics and as inhibitors of enzymes breaking down connective tissue, in particular granulocyte elastase.

  本发明涉及式 (I) 的杂环氨基甲酸酯类化合物 其中 a) X 表示基团 CR⁴，Y 表示基团 CR⁵，其中 R¹ 代表 C₁- 至 C₆- 低级烷基、取代的 C₁- 至 C₆- 低级烷基、芳基-C₁- 至 C₆- 低级烷基、芳基或杂环基、 R² 和 R³ 各自代表以下含义的基团： 氢原子、C₁- 至 C₆-低级烷基、C₁- 至 C₆-低级烷氧基、C₁- 至 C₆-低级硫代烷基、卤素原子、硝基、羟基、三氟甲基、氰基、磺基、C₁-至 C₆- 低级烷基磺酰基、羧酸基、C₁-至 C₆- 低级烷氧基羰基、C₁-至 C₆- 低级烷氧基羰氧基、乙酰胺基、苯甲酰胺基或基团 -N(R⁶)R⁷、 R⁴ 和 R⁵ 各自代表氢原子、C₁- 至 C₆- 低级烷基、取代的 C₁- 至 C₆- 低级烷基、芳基-C₁- 至 C₆- 低级烷基或芳基、 m 和 n 各自等于 0、1、2、3 或 4，以及 R⁶ 和 R⁷ 相互独立地代表氢原子或 C₁- 至 C₆- 低级烷基、 或其中 b) X 和 Y 表示氮原子，其中 m、n、R¹、R²、R³、R⁶ 和 R⁷ 具有 a) 项所述的含义、 但 R¹ 不是乙基，如果 R¹ 表示甲基、未取代的 C₃- 至 C₆- 低级烷基、苯基或苄基，则至少有一个 R² 或 R³ 基不同于氢原子或卤素原子、 或其中 c) X 表示氮原子，Y 表示 CR⁵ 基，其中 R¹ 代表取代的 C₁- 至 C₆- 低级烷基、芳基-C₁- 至 C₆- 低级烷基、芳基或杂环基、 R⁵ 代表氢原子或 C₁- 至 C₆- 低级烷基，以及 m、n、R²、R³、R⁶ 和 R⁷ 具有 a) 项中所述的含义、 或其中 d) X 表示氮原子，Y 表示 CR⁵ 基，其中 R⁵ 代表取代的 C₁- 至 C₆- 低级烷基、芳基-C₁- 至 C₆- 低级烷基或芳基，以及 m、n、R¹、R²、R³、R⁶ 和 R⁷ 具有 a) 项中所述的含义、 或其中 e) Y 表示氮原子，X 表示基 CR⁴，其中 R⁴ 代表取代的 C₁- 至 C₆- 低级烷基或通式 (II) 的基团 -Z-R⁸（II） 其中 Z 代表羰基或羧基、硫原子或氧原子，以及 R⁸ 代表 C₁- 至 C₆- 低级烷基、取代的 C₁- 至 C₆- 低级烷基、芳基-C₁- 至 C₆- 低级烷基或芳基，以及 m、n、R¹、R²、R³、R⁶ 和 R⁷ 具有 a) 项中所述的含义、 或其中 f) Y 表示氮原子，X 表示基团 CR⁴，其中 R¹ 代表取代的 C₁- 至 C₆- 低级烷基、芳基或杂环基、 R⁴ 代表氢原子、C₁- 至 C₆- 低级烷基、取代的 C₁- 至 C₆- 低级烷基、取代的 C₁- 至 C₆- 低级烷基、芳基-C₁- 至 C₆- 低级烷基或芳基，以及 m、n、R²、R³、R⁶ 和 R⁷ 具有 a) 项中所述的含义、 但如果 R²、R³ 和 R⁴ 表示氢原子，则 R¹ 与未取代的苯基基不同、 以及 它们与生理上可承受的酸和碱的盐、 以及它们作为抗血栓药和分解结缔组织的酶抑制剂（尤其是粒细胞弹性蛋白酶）的用途。
• NOVEL AMINOBENZAMIDE DERIVATIVE
  申请人：BANYU PHARMACEUTICAL CO., LTD.

  公开号：EP1496052A1

  公开（公告）日：2005-01-12

  This invention relates to a novel compound represented by the formula (I): or a pharmaceutically acceptable salt thereof,    wherein    R1 is -S(O)p-A, -S-(O)q-B or -O-D, wherein p and q, which are the same or different, each represent an integer from 0 to 2, A is a straight chain C1-C10 alkyl group which may be substituted by R10, and B and D each independently represent R12 which may be substituted by R10;    R2 is a hydrogen atom, a halogen atom, or a straight chain or branched C1-C6 alkyl group which may be substituted by R10;    X1 and X2 each independently represent N or CH, but cannot both be N;    the formula (II): shows a monocyclic or bicyclic heteroaryl group which has a nitrogen atom adjacent to the carbon atom bonded to the amide group, and the heteroaryl group may be substituted by R10;    R10 is R11, or a hydrocarbon group which may be substituted by R11;    R11 is, for example, a hydrogen atom or amino; and    R12 is, for example, phenyl, thiazolyl, pyridyl or methylene dioxyphenyl. The compound according to this invention has a glucokinase activation effect, and for example, is useful in the treatment and prevention of diabetes mellitus, and in the prevention of its complications such as diabetic nephropathy, diabetic retinopathy, diabetic neuropathy and diabetic arteriosclerosis.

  本发明涉及一种由式(I)代表的新型化合物： 或其药学上可接受的盐、 其中 R1是-S(O)p-A、-S-(O)q-B或-O-D，其中p和q相同或不同，各自代表0至2的整数，A是可被R10取代的直链C1-C10烷基，B和D各自独立地代表可被R10取代的R12； R2 是氢原子、卤素原子或可被 R10 取代的直链或支链 C1-C6 烷基； X1 和 X2 各自独立地代表 N 或 CH，但不能都是 N； 式 (II)： 表示单环或双环杂芳基，该杂芳基具有一个与酰胺基键合的碳原子相邻的氮原子，该杂芳基可被 R10 取代； R10 是 R11，或可被 R11 取代的烃基； R11 例如是氢原子或氨基；以及 R12 例如是苯基、噻唑基、吡啶基或亚甲基二氧苯基。 根据本发明的化合物具有葡萄糖激酶活化作用，例如，可用于治疗和预防糖尿病，以及预防其并发症，如糖尿病肾病、糖尿病视网膜病变、糖尿病神经病变和糖尿病动脉硬化。
• 10.1021/acs.orglett.4c01337
  作者：Zhao, Lulu、Hu, Pengwei、Tian, Jian、Zhang, Xiao、Yang, Chao、Guo, Lin、Xia, Wujiong

  DOI：10.1021/acs.orglett.4c01337

  日期：——

  sustainable electrochemical method for the synthesis of cyclic ethers and acyclic aldehydes from alkanols has been reported. This strategy has been successfully applied to cycloalkanols bearing different ring sizes and different types of nucleophiles. In addition, mechanistic investigations show that the reactions undergo sequential processes, including anodic oxidation, β-scission, and nucleophilic addition

  报道了一种从烷醇合成环醚和无环醛的有效且可持续的电化学方法。该策略已成功应用于具有不同环尺寸和不同类型亲核试剂的环烷醇。此外，机理研究表明反应经历连续过程，包括阳极氧化、β-断裂和亲核加成。该方法为从环烷醇和亲核试剂构建环醚和末端醛提供了一种新的合成方法。