2-chloro-5-S-benzyl-thioaniline | 917894-06-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-chloro-5-S-benzyl-thioaniline
• 英文别名: 5-(benzylthio)-2-chloroaniline；5-benzylthio-2-chloroaniline；5-(Benzylsulfanyl)-2-chloroaniline；5-benzylsulfanyl-2-chloroaniline
• CAS: 917894-06-5
• 化学式: C₁₃H₁₂ClNS
• 分子量: 249.764
• InChiKey: KHQWQWCIYFTLEL-UHFFFAOYSA-N

物化性质

• 沸点：
  393.4±42.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  16
• 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：
  51.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-chloro-5-S-benzyl-thioaniline 在 盐酸 、 aluminum (III) chloride 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 6.0h， 生成 N-(2-chloro-5-mercaptophenyl)-N'-(3-methylthiophenyl)-N'-methyl-guanidine hydrochloride
  参考文献：
  名称：

  WO2006/136846

  摘要：

  公开号：
• 作为产物：
  描述：

  4-氯-3-硝基苯磺酰氯 在 盐酸 、 tin(II) chloride dihdyrate 、 potassium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 2-chloro-5-S-benzyl-thioaniline
  参考文献：
  名称：

  N′-3-(Trifluoromethyl)phenyl Derivatives of N-Aryl-N′-methylguanidines as Prospective PET Radioligands for the Open Channel of the N-Methyl-d-aspartate (NMDA) Receptor: Synthesis and Structure–Affinity Relationships

  摘要：

  N-Methyl-D-aspartate (NMDA) receptor dysfunction has been linked to several neuropsychiatric disorders, including Alzheimer's disease, epilepsy, drug addiction, and schizophrenia. A radioligand that could be used with PET to image and quantify human brain. NMDA receptors in the activated "open channel" state would be useful for research on such disorders and for the development of novel therapies,: To date, no radioligands have Shown well-validated efficacy for imaging NMDA receptors in human subjects. In order to discover improved radioligands for PET imaging, we explored structure affinity relationships in N'-3-(trifluoromethyl)phenyl derivatives of N-aryl-N'-methylguanidines, seeking high affinity and moderate lipophilicity, plus necessary amenability for labeling with a positron-emitter, either carbon-11 or fluorine-18. Among a diverse set of 80 prepared N'-3-(trifluoromethyl)phenyl derivatives, four of these compounds (13, 19, 20, and 36) displayed desirable low nanomolar affinity for inhibition of [H-3](+)-MK801 at the PCP binding site and are of interest for candidate PET radioligand development.

  DOI：

  10.1021/acs.jmedchem.5b01510

文献信息

• Synthesis and in vitro evaluation of 18F-labelled S-fluoroalkyl diarylguanidines: Novel high-affinity NMDA receptor antagonists for imaging with PET
  作者：Edward G. Robins、Yongjun Zhao、Imtiaz Khan、Anthony Wilson、Sajinder K. Luthra、Erik Årstad

  DOI：10.1016/j.bmcl.2010.01.052

  日期：2010.3

  Two S-[18F]fluoroalkylated diarylguanidines were synthesized and evaluated in vitro as potential tracers for imaging of N-methyl-d-aspartate receptors (NMDARs) with positron emission tomography (PET). [18F]1 and [18F]10 were synthesized by [18F]fluoroethylation and [18F]fluoromethylation of the thiol precursor 6, respectively. [18F]1 is a promising candidate NMDAR PET tracer, with low nanomolar affinity

  两个小号- [ 18 F]氟烷基diarylguanidines合成和体外评价为成像潜在示踪剂Ñ甲基d天冬氨酸受体（NMDAR的）与正电子发射断层扫描（PET）。通过硫醇前体6的[ 18 F]氟乙基化和[ 18 F]氟甲基化分别合成[ 18 F] 1和[ 18 F] 10。[ 18 F] 1是一种有前途的候选NMDAR PET示踪剂，对NMDA PCP部位的纳摩尔亲和力低，选择性高且亲脂性中等。
• IMAGING 18F OR 11C-LABELLED ALKYLTHIOPHENYL GUANIDINES
  申请人：Robins Edward George

  公开号：US20100143252A1

  公开（公告）日：2010-06-10

  The invention provides a compound of formula (I); or a salt or solvate thereof, wherein: R 1 is hydrogen or C 1-4 alkyl; R 2 and R 4 are each independently selected from C 1-4 alkyl, [ 11 C] C 1-4 alkyl, and [ 18 F]—C 1-4 fluoroalkyl provided that at least one of R 2 and R 4 is [ 11 C] C 1-4 alkyl or [ 18 F]—C 1-4 fluoroalkyl; and R 3 is halo. Such compounds having use for imaging central nervous system receptors.

  本发明提供了式（I）的化合物；或其盐或溶剂，其中：R1为氢或C1-4烷基；R2和R4各自独立地选自C1-4烷基，[11C] C1-4烷基和[18F] -C1-4氟代烷基，但要求R2和R4中至少有一个是[11C] C1-4烷基或[18F] -C1-4氟代烷基；以及R3为卤素。这种化合物可用于成像中枢神经系统受体。
• Nitrogenated fused ring derivative, pharmaceutical composition comprising the same, and use of the same for medical purposes
  申请人：Kissei Pharmaceutical Co., Ltd.

  公开号：US08217069B2

  公开（公告）日：2012-07-10

  [Purpose] The present invention provides compounds useful as agents for the prevention or treatment of a sex hormone-dependent disease or the like. [Solution] The present invention provides nitrogen-containing fused ring derivatives represented by the following general formula (I) which has a GnRH antagonistic activity, prodrugs, salts, pharmaceutical compositions containing the same, medicinal uses thereof and the like. In the formula (I), rings A and B are independently aryl or heteroaryl; RA and RB are independently halogen, cyano, alkyl, alkylsulfonyl, —OW1, —SW1, —COW2, —NW3W4, —SO2NW3W4, aryl, etc.; RC is H or alkyl; E is oxygen atom, etc.; U is single bond or alkylene; and X is Y, —CO—Y, —SO2—Y, —S-(alkylene)-Y, —O-(alkylene)-Y, —SO2-(alkylene)-Y, etc.; Y is Z or amino, etc.; and Z is cycloalkyl, heterocycloalkyl, aryl, heteroaryl, etc.

  [目的] 本发明提供一种化合物，可用作预防或治疗性激素依赖性疾病或类似疾病的药物。 [解决方案] 本发明提供一种氮杂环融合衍生物，其表示为以下通式（I），具有GnRH拮抗活性，包括前药、盐、含有该化合物的制药组合物、药用用途等。 在式（I）中，环A和环B分别是芳基或杂芳基；RA和RB分别是卤素、氰基、烷基、烷基磺酰基、—OW1、—SW1、—COW2、—NW3W4、—SO2NW3W4、芳基等；RC是氢或烷基；E是氧原子等；U是单键或烷基；X是Y、—CO—Y、—SO2—Y、—S-（烷基）-Y、—O-（烷基）-Y、—SO2-（烷基）-Y等；Y是Z或氨基等；Z是环烷基、杂环烷基、芳基、杂芳基等。
• NITROGENATED FUSED RING DERIVATIVE, PHARMACEUTICAL COMPOSITION COMPRISING THE SAME, AND USE OF THE SAME FOR MEDICAL PURPOSES
  申请人：Kissei Pharmaceutical Co., Ltd.

  公开号：EP2143724B1

  公开（公告）日：2013-12-11
• FUSED HETEROCYCLIC DERIVATIVE, MEDICINAL COMPOSITION CONTAINING THE SAME, AND MEDICINAL USE THEREOF
  申请人：Kissei Pharmaceutical Co., Ltd.

  公开号：EP1939204B3

  公开（公告）日：2022-08-24