N-methyl-N'-3-methoxyphenylthiourea | 35524-92-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-methyl-N'-3-methoxyphenylthiourea
• 英文别名: 1-(3-methoxyphenyl)-3-methylthiourea；[(3-Methoxyphenyl)amino](methylamino)methane-1-thione
• CAS: 35524-92-6
• 化学式: C₉H₁₂N₂OS
• mdl: MFCD02940763
• 分子量: 196.273
• InChiKey: QIYDZWGMJFYMGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  65.4
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-methyl-N'-3-methoxyphenylthiourea 在 盐酸 、 sodium nitrite 作用下， 反应 1.0h， 生成 3-N,5-N-bis(3-methoxyphenyl)-2,4-dimethyl-1,2,4-thiadiazolidine-3,5-diimine
  参考文献：
  名称：

  Pandeya, Surendra N.; Naik, Praful R., Journal of the Indian Chemical Society, 1996, vol. 73, # 7, p. 363 - 365

  摘要：

  DOI：
• 作为产物：
  描述：

  3-甲氧基苯异氰酸 在 tetraphosphorus decasulfide 、 1,4-环己二烯 、 叠氮基三甲基硅烷 、 四丁基溴化铵 、 sodium hydroxide 作用下， 以 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 1.0h， 生成 N-methyl-N'-3-methoxyphenylthiourea
  参考文献：
  名称：

  Clean Photodecomposition of 1-Methyl-4-phenyl-1H-tetrazole-5(4H)-thiones to Carbodiimides Proceeds via a Biradical

  摘要：

  The photochemistry of 1-methyl-4-phenyl-1H-tetrazole-5(4H)-thione (la) and 1-(3-methoxyphenyl)4-methyl-1H-tetrazole-5(4H)-thione (1b) was studied in acetonitrile at 254 and 300 nm, which involves expulsion of dinitrogen and sulfur to form the respective carbodiimides 5a,b as sole photoproducts. Photolysis of the title compounds in the presence of 1,4-cyclohexadiene trap led to the formation of respective thioureas, providing strong evidence for the intermediacy of a 1,3-biradical formed by the loss of dinitrogen. In contrast, a trapping experiment with cyclohexene provided no evidence to support an alternative pathway of photodecomposition involving initial desulfurization followed by loss of dinitrogen via the intermediacy of a carbene. Triplet sensitization and triplet quenching studies argue against the involvement of a triplet excited state. While the quantum yields for the formation of the carbodiimides 5a,b were modest and showed little change on going from a C6H5 (1a) to mOMeC(6)H(4) (1b) substituent on the tetrazolethione ring, the highly clean photodecomposition of these compounds to a photostable end product makes them promising lead structures for industrial, agricultural, and medicinal applications.

  DOI：

  10.1021/jo1019859

文献信息

• Efficient Conversion of Substituted Aryl Thioureas to 2-Aminobenzothiazoles Using Benzyltrimethylammonium Tribromide
  作者：Alfonzo D. Jordan、Chi Luo、Allen B. Reitz

  DOI：10.1021/jo0349431

  日期：2003.10.1

  The reaction of molecular bromine (Br2) with arylthioureas is known to produce 2-aminobenzothiazoles (Hugerschoff reaction). We show here that benzyltrimethylammonium tribromide (1, PhCH2NMe3Br3), a stable, crystalline organic ammonium tribromide (OATB), can be readily utilized as an alternative electrophilic bromine source. It is easier to control the stoichiometry of addition with an OATB, which

  已知分子溴（Br2）与芳基硫脲反应生成2-氨基苯并噻唑（Hugerschoff反应）。我们在这里显示了三溴苄基三甲基铵（1，PhCH2NMe3Br3），一种稳定的结晶有机三溴化铵（OATB），可以很容易地用作替代的亲电子溴源。用OATB更容易控制添加的化学计量，从而最大程度地减少了由过量试剂引起的芳香族溴化反应。我们已经开发了一种直接程序，该程序可以使用四丁基硫氰酸铵（Bu4NSCN）和PhCH2NMe3Br3从异硫氰酸酯和胺中制备官能化的2-氨基苯并噻唑。
• Neurodegenerative therapies
  申请人：LYTIX BIOPHARMA AS

  公开号：US10231954B2

  公开（公告）日：2019-03-19

  The present invention provides a compound of formula (I) wherein: Y represents a C or N atom which may be substituted or form a cyclic group with R″′ but may not be a quaternary C atom; R′ is —OR1, —CONH2, —CF3, F, —OH, —NO2, —CN or —OCOR1 in which R1, is C1-3 alkyl and each may be in the beta or gamma position; R″ is C1-3 alkyl or H; and R″′ is H or a group consisting of 1-12 non-hydrogen atoms and may be linear, branched and/or incorporate one or more cyclic groups, cyclic groups may be aromatic and/or heterocyclic and 2 or more cyclic groups may be linked or fused and each may be substituted; or a salt, hydrate or solvate of a compound of formula (I) for use in the treatment or prevention of a neurodegenerative disorder by inhibiting formation of neurofibrillary (tau) tangles and/or by inhibiting Dyrk 1A. The invention further relates to non-therapeutic uses of these compounds.

  本发明提供了式(I)化合物，其中：Y 代表 C 原子或 N 原子，可被 R″′ 取代或与 R″′ 形成环状基团，但不得是季 C 原子；R′为-OR1、-CONH2、-CF3、F、-OH、-NO2、-CN 或-OCOR1，其中 R1 为 C1-3 烷基，且各可位于β或γ位；R″为 C1-3 烷基或 H；和 R″′ 是 H 或由 1-12 个非氢原子组成的基团，可以是直链、支链和/或包含一个或多个环状基团，环状基团可以是芳香族和/或杂环基团，2 个或多个环状基团可以连接或融合，每个环状基团可以被取代；或式 (I) 化合物的盐、水合物或溶液，用于通过抑制神经纤维（tau）缠结的形成和/或通过抑制 Dyrk 1A 来治疗或预防神经退行性疾病。本发明还涉及这些化合物的非治疗用途。
• Naik; Pandeya, Bollettino Chimico Farmaceutico, 1994, vol. 133, # 5, p. 289 - 293
  作者：Naik、Pandeya

  DOI：——

  日期：——
• Chiral cyclic beta-amino acids and their derivates, pharmaceutical compositions containing them and the use of such compounds
  申请人：Bioblocks Magyarország Gyógyszerkémiai És Fejleszto KFT

  公开号：EP2102147B1

  公开（公告）日：2011-06-22
• Chiral Cyclic Beta-Amino Acids and their Derivatives, Pharmaceutical Compositions Containing Them and the Use of Such Compounds
  申请人：Fulop Ferenc

  公开号：US20100081717A1

  公开（公告）日：2010-04-01

  The invention relates to chiral cyclic β-amino acids of Formula (I) and their salts formed with pharmaceutically acceptable acids or bases, wherein the main meanings of the substituents are as follows: R stands for C 1-4 Alk; X stands for —COOH, —CONH 2 , —CONH(C 1-4 Alk), —CON(C 1-4 Alk) 2 , —COO(C 1-4 Alk), —COPhe-O-(C 1-4 Alk) or —CH 2 OH; Y stands for —NH 2 , —NHBoc, —NHFmoc, —NH(C 1-4 Alk), —N(C 1-4 Alk) 2 , —NHCH 2 Ph, or Ar—NH—C(=X 0 )—N(R 0 )— wherein Ar stands for a phenyl group substituted by C 1-4 alkoxy or halogen, X 0 stands for O or S, and R 0 stands for hydrogen or benzyl; and X+Y stands for —CONH— vagy —CON(Boc)-; with the proviso that when X stands for —COOH, then Y may be only different from —NH 2 . The invention also relates to pharmaceutical compositions having multidrug-resistance reversing effect that contain one or more compound(s) of Formula (I) or a salt thereof and inert pharmaceutical carriers and/or auxiliary agents. The invention also relates to carboxylic acids of Formula (XX) and their salts.