3-benzoyl-1-methyl-1H-1,2,4-triazole | 153334-39-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-benzoyl-1-methyl-1H-1,2,4-triazole
• 英文别名: (1-Methyl-1H-1,2,4-triazol-3-yl)phenylmethanone；(1-methyl-1,2,4-triazol-3-yl)-phenylmethanone
• CAS: 153334-39-5
• 化学式: C₁₀H₉N₃O
• 分子量: 187.201
• InChiKey: IXGATAIAVUFNMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  47.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-benzoyl-1-methyl-5-phenylthio-1H-1,2,4-triazole 在 Raney nickel (W₂-type) 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 3-benzoyl-1-methyl-1H-1,2,4-triazole
  参考文献：
  名称：

  Synthesis and Application of Triazole Derivatives. Synthesis of 3- and 5-Acyl-1,2,4-triazoles via Lithiation of 1-Alkyl-1H-1,2,4-triazoles.

  摘要：

  N-未取代的3-酰基-1H-1, 2, 4-三唑 (3) 和5-酰基-1-烷基-1H-1, 2, 4-三唑 (4) 通过5-锂三唑与酰胺的酰基化反应合成。1-甲基-5-苯硫基-1H-1, 2, 4-三唑 (11) 的3位通过锂化剂锂-2, 2, 6, 6-四甲基哌啶对其进行锂化，随后用酰胺对生成的负离子进行酰基化，并用Raney镍进行脱硫反应得到3-酰基衍生物 (5)。结构异构体3-酰基-4-烷基-4H-1, 2, 4-三唑 (6) 是通过对3进行N-甲基化反应制备的。

  DOI：

  10.1248/cpb.41.1226

文献信息

• AZOLE NUCLEOSIDES AND USE AS INHIBITORS OF RNA AND DNA VIRAL POLYMERASES
  申请人：Arterburn Jeffrey B.

  公开号：US20100129317A1

  公开（公告）日：2010-05-27

  Azole nucleosides represented by the formulae (I) and (II); wherein A=C or N B═C or N X═H; C 1 -C 6 alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, aryl, heterocyclo, halogen such as F, Cl, Br and I; OH, NH 2 , NH—(C 1 -C 6 alkyl, cycloalkyl, aryl or heterocyclo); Z═H; C 1 -C 6 alkyl, cycloalkyl, alkynyl, aryl, heterocyclo, halogen such as F, Cl, Br, I; OH NH 2 , NH—(C 1 -C 6 alkyl, cycloalkyl, aryl or heterocyclo; E=(CH 2 )HONHR; n is an interger from 0-6 and more typically 0-3; R 1= aryl or heterocyclo; each of W, Y, R is individually selected from the group consisting of H; C 1 -C 6 alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, aryl, heterocyclo, halogen such as F, Cl, Br, and I; O, OH, Oalkyl, Oaryl, NH 2 , NH(C 1 -C 6 alkyl, cycloalkyl, aryl or heterocyclo); provided that at least one of W, Y, and R is other than H and wherein both W and Y together can be ═O; and each D individually is OH, Oalkyl, Oaryl, FL and H; pharmaceutically acceptable salts thereof, prodrugs thereof and mixtures thereof are provided. Compounds of this disclosure are useful as inhibitors of viral RNA and DNA polymerases such as, but not limited to, Influenza, hantaan Virus, Crimean Congo hemorrhagic fever virus, hepatitis B, hepatitis C, Polio, Coxsackie A and B, Rhino, Echo, orthopoxvirus (small pox), HIV, Ebola, and West Nile virus polymerases; and especially orthopoxvirus, HIV, and hepatitis B.
• [EN] AZOLE NUCLEOSIDES AND USE AS INHIBITORS OF RNA AND DNA VARIAL POLYMERASES<br/>[FR] NUCLEOSIDES D'AZOLE ET UTILISATION EN TANT QU'INHIBITEURS DE POLYMERASES D'ARN ET D'ADN VIRAL
  申请人：SOUTHERN RES INST

  公开号：WO2008067002A2

  公开（公告）日：2008-06-05

  (EN) Azole nucleosides represented by the formulae (I) and (II); wherein A = C or N B = C or N X = H; C1-C6 alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, aryl, heterocyclo, halogen such as F, C1, Br and I; OH, NH2, NH-(C1-C6 alkyl, cycloalkyl, aryl, or heterocyclo); Z = H; C1-C6 alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, aryl, heterocyclo, halogen such as F, Cl, Br, I; OH, NH2, NH-(C1-C6 alkyl, cycloalkyl, aryl, or heterocyclo; E= (CH2)HONHR1; n is an integer from 0-6 and more typically 0-3; R1= aryl or heterocyclo; each of W, Y, R is individually selected from the group consisting of H; C1-C6 alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, aryl, heterocyclo; halogen such as F, Cl, Br, and I; O, OH, Oalkyl, Oaryl, NH2, NH-(C1-C6 alkyl, cycloalkyl, aryl, or heterocyclo); provided that at least one of W, Y, and R is other than H and wherein both W and Y together can be =O; and each D individually is OH, Oalkyl, Oaryl, Fl and H;pharmaceutically acceptable salts thereof, prodrugs thereof and mixtures thereof are provided. Compounds of this disclosure are useful as inhibitors of viral RNA and DNA polymerases such as, but not limited to, Influenza, Hantaan Virus, Crimean Congo hemorrhagic fever virus, hepatitis B, hepatitis C, Polio, Coxsackie A and B, Rhino, Echo, orthopoxvirus (small pox), HIV, Ebola, and West Nile virus polymerases; and especially orthopoxvirus, HIV, and hepatitis B.(FR) L'invention concerne des nucléosides d'azole représentés par les formules (I) et (II) ; dans lesquelles A = C ou N B = C ou N X = H ; alkyle, cycloalkyle, alcényle, cycloalcényle, alkynyle, aryle C1-C6, hétérocyclo, halogène tels que F, C1, Br et I ; OH, NH2, NH-(alkyle, cycloalkyle, aryle C1-C6 ou hétérocyclo) ; Z = H ; alkyle, cycloalkyle, alcényle, cycloalcényle, alkynyle, aryle C1-C6, hétérocyclo, halogène tels que F, Cl, Br, I ; OH, NH2, NH-(alkyle, cycloalkyle, aryle C1-C6 ou hétérocyclo) ; E= (CH2)HONHR1 ; n est un entier compris 0 et 6 et plus généralement entre 0 et 3 ; R1= aryle ou hétérocyclo ; W, Y, R sont choisis individuellement dans le groupe constitué par H ; alkyle, cycloalkyle, alcényle, cycloalcényle, alkynyle, aryle C1-C6, hétérocyclo ; halogène tels que F, Cl, Br et I ; O, OH, Oalkyle, Oaryle, NH2, NH-(alkyle, cycloalkyle, aryle C1-C6 ou hétérocyclo) ; à condition qu'au moins W, Y ou R soit autre que H, W et Y pouvant être ensemble =O ; et chaque D représente individuellement OH, Oalkyle, Oaryle, Fl et H ; des sels pharmaceutiquement acceptables, des promédicaments et des mélanges de ceux-ci. Les composés selon l'invention sont utiles en tant qu'inhibiteurs de polymérases d'ARN et d'ADN viral telles que, entre autres, les polymérases de la grippe, du virus Hantaan, du virus de la fièvre hémorragique de Crimée-Congo, de l'hépatite B, de l'hépatite C, de la polio, de Coxsackie A et B, de Rhino, d'Echo, de l'orthopoxvirus (variole), du VIH, d'Ebola et du virus du Nil occidental ; et en particulier de l'orthopoxvirus, du VIH et de l'hépatite B.
• Synthesis and Application of Triazole Derivatives. Synthesis of 3- and 5-Acyl-1,2,4-triazoles via Lithiation of 1-Alkyl-1H-1,2,4-triazoles.
  作者：Shunsaku OHTA、Ikuo KAWASAKI、Akihisa FUKUNO、Masayuki YAMASHITA、Toshiji TADA、Tetsuo KAWABATA

  DOI：10.1248/cpb.41.1226

  日期：——

  N-Unsubstituted 3-acyl-1H-1, 2, 4-triazoles (3), and 5-acyl-1-alkyl-1H-1, 2, 4-triazoles (4) were synthesized by acylation of 5-lithiotriazoles with amides. The 3-position of 1-methyl-5-phenylthio-1H-1, 2, 4-triazole (11) was lithiated by lithium 2, 2, 6, 6-tetramethylpiperidide, and acylation of the produced carbanion with amides followed by desulfurization with Raney nickel give the 3-acyl derivatives (5). The structural isomers, 3-acyl-4-alkyl-4H-1, 2, 4-triazoles (6), were prepared by N-methylation of 3.

  N-未取代的3-酰基-1H-1, 2, 4-三唑 (3) 和5-酰基-1-烷基-1H-1, 2, 4-三唑 (4) 通过5-锂三唑与酰胺的酰基化反应合成。1-甲基-5-苯硫基-1H-1, 2, 4-三唑 (11) 的3位通过锂化剂锂-2, 2, 6, 6-四甲基哌啶对其进行锂化，随后用酰胺对生成的负离子进行酰基化，并用Raney镍进行脱硫反应得到3-酰基衍生物 (5)。结构异构体3-酰基-4-烷基-4H-1, 2, 4-三唑 (6) 是通过对3进行N-甲基化反应制备的。