N-benzyl-2-thioxo-1,2-dihydropyridine-3-carboxamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-benzyl-2-thioxo-1,2-dihydropyridine-3-carboxamide
• 英文别名: N-benzyl-2-sulfanylidene-1H-pyridine-3-carboxamide
• 化学式: C₁₃H₁₂N₂OS
• 分子量: 244.317
• InChiKey: NSOAUNRMNHDPGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  73.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-benzyl-2-thioxo-1,2-dihydropyridine-3-carboxamide 在 劳森试剂 、 tetraphosphorus decasulfide 、 硫化氢 、 mercury(II) diacetate 、 碘 、 碳酸氢钠 、 溶剂黄146 作用下， 以 乙醇 、 氯仿 、 甲苯 、 xylene 为溶剂， 反应 18.5h， 生成 3H-[1,2]-dithiolo[3,4-b]pyridine-3-thione
  参考文献：
  名称：

  3H-[1,2]Dithiolo[3,4-b]pyridine-3-thione and its derivatives Synthesis and antimicrobial activity

  摘要：

  A series of 2-substituted isothiazolo[5,4-b]pyridine-3(2H)-thiones isothiazolo[5,4-b]pyridin-3(2H)-ones, N-substituted 2-sulfanylnicotinamides and the corresponding carbothioamide derivatives were synthesized and evaluated for their antimicrobial activity against several strains of Gram + and Gram - bacteria and fungi. Chemical syntheses were resumed into a comprehensive cyclic route that enables the reversible conversion for each derivative of the series considered. Among the tested compounds the N-(aralkyl)-2-sulfanylnicotinamides show the highest fungitoxicity (MIC = 1.25-5 mug/ml). The best activity towards Gram-positive bacteria was in the range of 2.5-5 mug/ml. Activity against Gram-negative bacteria was generally very poor for all compounds. (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(00)00084-7
• 作为产物：
  描述：

  N-苄基-2-氯烟酰胺 在 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 N-benzyl-2-thioxo-1,2-dihydropyridine-3-carboxamide
  参考文献：
  名称：

  Dunn, Allan D.; Norrie, Robert, Zeitschrift fur Chemie, 1988, vol. 28, # 7, p. 248 - 249

  摘要：

  DOI：

文献信息

• Process for depigmenting keratin materials using thiopyridinone compounds
  申请人：L'OREAL

  公开号：US11052028B2

  公开（公告）日：2021-07-06

  The invention relates to cosmetic processes and compositions for depigmenting, lightening and/or whitening keratin materials, in particular the skin, which comprises the application of a cosmetic composition comprising thiopyridinone compounds to keratin materials.

  本发明涉及用于脱色、淡化和/或美白角质材料（尤其是皮肤）的化妆品工艺和组合物，其中包括将包含噻啶酮化合物的化妆品组合物用于角质材料。
• N-Unsubstituted Sulfenamides by Electrophilic Amination of mercapto compounds
  作者：Siegfried Andreae

  DOI：10.1002/prac.19973390129

  日期：——

  Potential mercapto compounds derived from electron deficient heterocycles as 2- and 4-thiouracils, pyridines and pyridine-1-oxide are aminated by the oxaziridine 1 to new sulfenamides (6, 9, 11 and 15 or the isothiazolo-pyridine 14) which add to phenylisocyanates forming sulfenylureas (7, 10, 12 and 16). Several other mercapto compounds gave disulfides. Attempts of oxidation of the sulfenamides and the sulfenylureas were unsuccessful. The methylmercapto compound 19 after amination was hydrolyzed to the sulfoxide 20.
• PROCESS FOR DEPIGMENTING KERATIN MATERIALS USING THIOPYRIDINONE COMPOUNDS
  申请人：L'Oréal

  公开号：EP2651897A1

  公开（公告）日：2013-10-23
• US9138392B2
  申请人：——

  公开号：US9138392B2

  公开（公告）日：2015-09-22
• [EN] PROCESS FOR DEPIGMENTING KERATIN MATERIALS USING THIOPYRIDINONE COMPOUNDS<br/>[FR] PROCÉDÉ DE DÉPIGMENTATION DE MATIÈRES KÉRATINIQUES AU MOYEN DE COMPOSÉS DE THIOPYRIDINONE
  申请人：OREAL

  公开号：WO2012080075A1

  公开（公告）日：2012-06-21

  The invention relates to a cosmetic process for depigmenting, lightening and/or whitening keratin materials, in particular the skin, which comprises the application of a cosmetic composition comprising a compound of formula (I): or its tautomer form of formula (I) in which: R1 and R2, which may be identical or different, denote a radical chosen from: a) a hydrogen atom; b) a C1-C20 alkyl group optionally interrupted with N, S or O, optionally substituted with one or more group(s) chosen from -OR3, -SR3, -NR3R4, -CONHR3; -COOR3; and an aryl group optionally substituted with one or more hydroxyls and/or with one or more C1-C8 alkoxy radicals;c) a C1-C8 alkyl group substituted with a C5-C12 aryl radical optionally substituted with one or more hydroxyls and/or with one or more C1-C8 alkoxy radicals; d) a phenyl group optionally substituted with one or more hydroxyls and/or with one or more C1-C8 alkoxy radicals; R3 denoting H or a C1-C5 alkyl group, R4 denoting H, a C1-C5 hydrocarbon-based group or an acetyl group; it being possible for R1 and R2 to form, with the nitrogen atom which bears them, a ring chosen from pyrrolidine, pyrroline, piperidine, piperazine, morpholine, thiomorpholine and azepine. The invention also relates to the cosmetic use of a compound (I) or (I) as a whitening, lightening and/or depigmenting agent for keratin materials.