3-methylsulfanyl-aniline; hydrochloride | 94855-95-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-methylsulfanyl-aniline; hydrochloride
• 英文别名: 3-Methylmercapto-anilin; Hydrochlorid；3-methylthiophenylamine hydrochloride；3-Methylsulfanylaniline;hydrochloride
• CAS: 94855-95-5
• 化学式: C₇H₉NS*ClH
• 分子量: 175.682
• InChiKey: IOKNGZWWQSLSQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.41
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  51.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-methylsulfanyl-aniline; hydrochloride 在 盐酸 、 sodium carbonate 、 间氯过氧苯甲酸 、 sodium nitrite 作用下， 以 二氯甲烷 为溶剂， 反应 7.66h， 生成 3-甲砜基苯腈
  参考文献：
  名称：

  Reaction of arylhalodiazirines with thiophenoxide: a redox process

  摘要：

  Phenylbromodiazirine reacts with thiophenoxide ion in methanol to give benzonitrile, benzamidine, ammonia, and diphenyl disulfide. The reaction is general for arylhalodiazirines, with electron-withdrawing groups on the aromatic ring exerting a small rate-enhancing effect. Three potential mechanisms are suggested for this redox process. These mechanisms include an N-sulfenylated diazirine, a diazirinyl radical, and a diazirinyl anion. Ring opening of these intermediates and subsequent transformations would lead to benzonitriles, benzamidine, and ammonia. A key intermediate in these transformations is PhSNH2, 32. This intermediate has been independently generated and found to rapidly convert to ammonia and diphenyl disulfide under the reaction conditions. Another proposed intermediate, N-(phenylthio)benzamidine, 38, has also been independently generated and subjected to the reaction conditions, where benzamidine and more diphenyl disulfide result. Theoretical calculations suggest the existence of isomeric diazirinyl anions. In addition to a diazirinyl ion with charge essentially on carbon, there is also an allylic-type ion with charge on the two nitrogen atoms. Single-electron reduction of a diazirinyl radical necessarily leads to a nitrogen-centered diazirinyl anion. Conversion of this anion to the carbon-centered diazirinyl anion is a forbidden process. These theoretical studies suggest that the diazirinyl anion may be a viable intermediate in solution.

  DOI：

  10.1021/ja00070a003
• 作为产物：
  描述：

  3-乙酰氨基茴香硫醚 在 盐酸 、 乙醇 作用下， 生成 3-methylsulfanyl-aniline; hydrochloride
  参考文献：
  名称：

  Zincke; Mueller, Chemische Berichte, 1913, vol. 46, p. 783

  摘要：

  DOI：
• 作为试剂：
  描述：

  3-氨基茴香硫醚 在 lithium hydroxide 、 3-methylsulfanyl-aniline; hydrochloride 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二苯醚 、 甲苯 为溶剂， 反应 1.0h， 生成 (1R,2S)-1-[[(2S,4R)-1-[(2S)-3,3-dimethyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoyl]-4-(7-methylsulfanyl-2-phenylquinolin-4-yl)oxypyrrolidine-2-carbonyl]amino]-2-ethenylcyclopropane-1-carboxylic acid
  参考文献：
  名称：

  A Systematic Approach to the Optimization of Substrate-Based Inhibitors of the Hepatitis C Virus NS3 Protease:  Discovery of Potent and Specific Tripeptide Inhibitors

  摘要：

  The inadequate efficacy and tolerability of current therapies for the infectious liver disease caused by the hepatitis C virus have warranted significant efforts in the development of new therapeutics. We have previously reported competitive peptide inhibitors of the NS3 serine protease based on the N-terminal cleavage products of peptide substrates. A detailed study of the interactions of these substrate-based inhibitors with the different subsites of the serine protease active site led to the discovery of novel residues that increased the affinity of the inhibitors. In this paper, we report the combination of the best binding residues in a tetrapeptide series that resulted in extremely potent inhibitors that bind exquisitely well to this enzyme. A substantial increase in potency was obtained with the simultaneous introduction of a 7-methoxy-2-phenyl-4-quinolinoxy moiety at the gamma-position of the P2 proline and a tert-leucine as a P3 residue. The increase in potency allowed for the further truncation and led to the identification of tripeptide inhibitors. Structure activity relationship studies on this inhibitor series led to the identification of carbamate-containing tripeptides that are able to inhibit replication of subgenomic HCV RNA in cell culture with potencies below 1 muM. This inhibitor series has the potential of becoming antiviral agents for the treatment of HCV infections.

  DOI：

  10.1021/jm0494523

文献信息

• Aminopyrazoline derivatives
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP0119449A1

  公开（公告）日：1984-09-26

  The compounds of formula (I) and their pharmacologically acceptable acid addition salts are useful in medicine. In formula (I) Y is a group selected from alkylthio, alkenylthio, arylthio, alkylsulphinyl, alkenylsulphinyl, arylsulphinyl, alkylsulphonyl, alkenylsulphonyl, arylsulphonyl, alkoxy, alkenyloxy, or aryloxy, in which group any hydrogen atom is optionally replaced by a halogen atom; each X is the same or different and is independently selected from alkylthio, alkenylthio, arylthio, alkylsulphinyl, arylsulphinyl, alkenylsulphinyl, alkylsulphonyl, alkenylsulphonyl, arylsulphonyl, alkoxy, alkenyloxy, aryloxy, alkyl, alkenyl, aryl, trihaloalkyl, or halogen; n is 0 to 4; R1 is hydrogen, alkyl, alkenyl, alkynyl, aralkyl or aryl; R2 is hydrogen, alkyl, acyl of 1-4 carbon atoms, aroyl of 6-10 carbon atoms or alkoxycarbonyl; or R1 and R2 together represent where X is a suitable substituent and m is 0-5; and R3and R4 are the same or different and each represents hydrogen or alkyl provided that when R1 is other than hydrogen, R2 is not acyl or aroyl.

  式（I）化合物及其药理上可接受的酸加成盐可用于医药。 在式 (I) 中 Y 是选自烷基硫基、烯基硫基、芳基硫基、烷基亚砜基、烯基亚砜基、芳基亚砜基、烷基磺酰基、烯基磺酰基、芳基磺酰基、烷氧基、烯氧基或芳氧基的基团，其中任何氢原子可选择被卤原子取代； 每个 X 相同或不同，且独立选自烷基硫基、烯基硫基、芳基硫基、烷基亚砜基、芳基亚砜基、烯基亚砜基、烷基亚砜基、烯基亚砜基、芳基亚砜基、烷氧基、烯氧基、芳氧基、烷基、烯基、芳基、三卤代烷基或卤素； n 为 0 至 4； R1 是氢、烷基、烯基、炔基、芳基或芳基； R2 是氢、烷基、1-4 个碳原子的酰基、6-10 个碳原子的芳基或烷氧基羰基；或 R1 和 R2 共同代表 其中 X 为合适的取代基，m 为 0-5；以及 R3 和 R4 相同或不同，各自代表氢或烷基 但当 R1 不是氢时，R2 不是酰基或芳基。
• WO2007/84786
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis and Pharmacological Evaluation of <i>N</i>-(2,5-Disubstituted phenyl)-<i>N</i>‘-(3-substituted phenyl)-<i>N</i>‘-methylguanidines As <i>N</i>-Methyl-<scp>d</scp>-aspartate Receptor Ion-Channel Blockers
  作者：Lain-Yen Hu、Junqing Guo、Sharad S. Magar、James B. Fischer、Kathleen J. Burke-Howie、Graham J. Durant

  DOI：10.1021/jm970459c

  日期：1997.12.1

  In the mammalian central nervous system, the N-methyl-D-aspartate (NMDA) subclass of glutamate receptors may play an important role in brain diseases such as stroke, brain or spinal cord trauma, epilepsy, and certain neurodegenerative diseases. Compounds which specifically antagonize the actions of the neurotransmitter glutamate at the NMDA receptor ion-channel site offer a novel approach to treating these disorders. CERESTAT (4, aptiganel CNS 1102) is currently undergoing clinical trial for the treatment of traumatic brain injury and stroke. Previously, we reported that analogues of N-1-naphthyl-N'-(3-ethylphenyl)-N'-methylguanidine (4) bound to the NMDA receptor ion-channel site with high potency and selectivity. Recently, molecules active at both a receptors and NMDA receptor sites were investigated. A series of substituted diphenylguanidines 6 which are structurally related to N-1-naphthyl-N'-(3-ethylphenyl)-N'-methylguanidine was prepared. Compounds containing appropriate substitution pattern in one of the phenyl rings of diphenylguanidines displayed high affinity. For example, N-(2,5-dibromophenyl)-N'-(3-ethylphenyl)-N'-methylguanidine (27b, R-2 = R-5 = Br, R-3 = C2H5) exhibited potency at both a receptors and NMDA receptor sites; 27b also showed high efficacy in vivo in a neonatal rat excitotoxicity model. Further studies indicated that substituent effects were important in this compound series, and 2,5-disubstituted phenyl was the preferred substitution pattern for high-affinity binding at NMDA receptor sites. Bromo and methylthio were the optimal substituents for the R-2 and R-5 positions of the 2,5-disubstituted phenyl group, respectively. N-(2-Bromo-5-(methylthio)phenyl)-N'-(3-ethylphenyl)- N'-methylguanidine (34b, R-2 = Br, R-5 = SMe, R-3 = C2H5) was highly active at NMDA receptor sites. We found that the binding affinity of guanidines of type 6 could be further enhanced with the appropriate substitution at R-3. Optimal activity in this series are afforded by 43b and 44b (R-2 = Cl or Br, R-5 = R-3 = SCH3). Both 43b and 44b bound to NMDA receptor sites with high potency and selectivity (K-i vs [H-3]MK-801: 1.87 and 1.65 nM, respectively); these compounds are active in vivo in various animal models of neuroprotection. The structure-activity relationships for-these compounds at the NMDA receptor ion-channel site are discussed.
• Syntheses, structures and characterizations of two organoimido derivatives of POMs containing sulfide groups
  作者：Hui Guo、Shang-Ze Li、Xin-Xing Xiong、Di Li、Zi-Yang Liu、Long-Sheng Wang、Ping-Fan Wu

  DOI：10.1016/j.poly.2015.02.010

  日期：2015.5

  Two remote methylthio group functionalized organoimido derivatives of hexamolybdate, (Bu4N)(2)[Mo6O18(NC6H4-SCH3-p)] (1) and (Bu4N)(2)[Mo6O18(NC6H4-SCH3-m)] (2), were synthesized through the refluxing reaction of octamolybdates, the hydrochloride salts of corresponding organic amines in anhydrous acetonitrile with dicyclohexylcarbodiimide (DCC) as dehydration agent. They are characterized by single crystal X-ray diffraction, FT-IR spectra, UV-Vis spectra, elemental analysis, H-1 NMR and cyclic voltammetry. X-ray structural study reveals that anion clusters of both compounds possess some typical structural features of mono-substituted hexamolybdate, and their anion clusters are connected into two dimensional network via intermolecular multiple C-H center dot center dot center dot O hydrogen bonds. (C) 2015 Elsevier Ltd. All rights reserved.
• Reaction of arylhalodiazirines with thiophenoxide: a redox process
  作者：Xavier Creary、Anthony F. Sky、Gillian Phillips、David E. Alonso

  DOI：10.1021/ja00070a003

  日期：1993.8

  Phenylbromodiazirine reacts with thiophenoxide ion in methanol to give benzonitrile, benzamidine, ammonia, and diphenyl disulfide. The reaction is general for arylhalodiazirines, with electron-withdrawing groups on the aromatic ring exerting a small rate-enhancing effect. Three potential mechanisms are suggested for this redox process. These mechanisms include an N-sulfenylated diazirine, a diazirinyl radical, and a diazirinyl anion. Ring opening of these intermediates and subsequent transformations would lead to benzonitriles, benzamidine, and ammonia. A key intermediate in these transformations is PhSNH2, 32. This intermediate has been independently generated and found to rapidly convert to ammonia and diphenyl disulfide under the reaction conditions. Another proposed intermediate, N-(phenylthio)benzamidine, 38, has also been independently generated and subjected to the reaction conditions, where benzamidine and more diphenyl disulfide result. Theoretical calculations suggest the existence of isomeric diazirinyl anions. In addition to a diazirinyl ion with charge essentially on carbon, there is also an allylic-type ion with charge on the two nitrogen atoms. Single-electron reduction of a diazirinyl radical necessarily leads to a nitrogen-centered diazirinyl anion. Conversion of this anion to the carbon-centered diazirinyl anion is a forbidden process. These theoretical studies suggest that the diazirinyl anion may be a viable intermediate in solution.