2-(4'-methyl-2'-nitrophenylthio)benzoic acid | 100726-00-9

• 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-(4'-methyl-2'-nitrophenylthio)benzoic acid
• 英文别名: 2-(4-Methyl-2-nitrophenylthio)benzoic acid；2-(4-methyl-2-nitrophenyl)sulfanylbenzoic acid
• CAS: 100726-00-9
• 化学式: C₁₄H₁₁NO₄S
• 分子量: 289.312
• InChiKey: AONXLRMVJCBOLL-UHFFFAOYSA-N

物化性质

• 熔点：
  189-191 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  445.0±40.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(4'-methyl-2'-nitrophenylthio)benzoic acid 在 盐酸 、 氯化亚砜 、 硼烷四氢呋喃络合物 、 potassium carbonate 、 tin(ll) chloride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 5.0h， 生成 N,N-dimethyl-2-(2-amino-4-methylphenylthio)benzylamine
  参考文献：
  名称：

  Fluorinated Diaryl Sulfides as Serotonin Transporter Ligands:  Synthesis, Structure−Activity Relationship Study, and in Vivo Evaluation of Fluorine-18-Labeled Compounds as PET Imaging Agents

  摘要：

  A series of new, fluorine-containing substituted diphenyl sulfides was synthesized to serve as candidate ligands for positron emission tomography (PET) imaging of the serotonin transporter (SERT) and to further probe the structure-activity relationship (SAR) of this class of compounds. Candidate compounds were assayed for their affinities to the monoamine transporters (SERT, norepinephrine transporter (NET), and dopamine transporter (DAT)) in competitive binding experiments in vitro using cloned human transporters. From these in vitro assays, four compounds (7c-f) were chosen for further evaluation. All four compounds have nanomolar affinity for SERT (K-i 1.46 nM, 1.04 nM,1.83 nM, and 3.58 nM for 7c, 7d, 7e, and 7f, respectively). The F-18-labeled compounds, 16 and 18a-c, were prepared via a two-step radiosynthesis. Biodistribution studies in rats indicated that the F-18-labeled compounds localized in brain regions with high concentrations of SERT. Furthermore, competition experiments demonstrated that the binding of these radioligands in the rat brain was saturable, specific, and selective to SERT. Specific binding in the rat hypothalamus peaked at 5.6 for ligand 16 and 4.4 for 18b at 90 min after radioactivity administration. For ligand 18a, this same ratio was 8.4 at 120 min postinjection, while compound 18c displayed a lower-specific binding ratio of 2.4. In summary, four F-18-labeled ligands were prepared and evaluated as candidate PET imaging agents for SERT. Among these four ligands, three appear to be promising radioligands suitable for the labeling of SERT in vivo, with 18a providing a higher specific binding in vivo than 16 or 18b.

  DOI：

  10.1021/jm0400808
• 作为产物：
  描述：

  ethyl 2-mercaptobenzoate 在 sodium hydroxide 、 copper(l) iodide 、 caesium carbonate 作用下， 以 甲苯 为溶剂， 反应 0.33h， 生成 2-(4'-methyl-2'-nitrophenylthio)benzoic acid
  参考文献：
  名称：

  N，N-二甲基-2-（2'-氨基-4'-取代的苯硫基）苄胺的合成，体外表征和放射性标记：潜在的候选物质，作为选择性5-羟色胺转运体的配体。

  摘要：

  制备了一系列在4'-苯基位置取代的N，N-二甲基-2-（2'-氨基-4'-碘苯硫基）苄胺的N，N-二甲基化和N-单甲基化类似物，并进行了体外评估血清素转运蛋白（SERT）的选择性。制备了几种衍生物，其中4'-位未被取代的13和33a或被甲基14a和33b，乙烯基14b和34，乙基16和35，羟甲基20和41，羟乙基22，氟乙基23，羟丙基27和氟丙基取代28.使用[（3）H]西酞普兰，[（3）H] WIN 35,428或[（125）I] RTI在稳定表达转染的人类SERT，多巴胺转运蛋白（DAT）和去甲肾上腺素转运蛋白（NET）的细胞中竞争结合-55和[（3）H] nisoxetine分别显示出以下顺序的SERT亲和力（K（i）（nM））：14a（0.25）> 16（0.49）> 20（0.57）> 14b（1.12）> 13（1.59）> 33b（1.94）= 35（2.04）>> 23（8

  DOI：

  10.1021/jm050079o

文献信息

• Process for preparing dibenzothiazepine compounds
  申请人：Murray Michael Paul

  公开号：US20070203336A1

  公开（公告）日：2007-08-30

  A dibenzothiazepine compound is suitably prepared by subjecting a 2-amino-2′-carboxy-diphenylsulfide compound to dehydration-condensation reaction in the presence of an acidic catalyst; the 2-amino-2′-carboxy-diphenylsulfide compound is suitably prepared by reducing a 2-nitro-2′-carboxy-diphenylsulfide compound in a lower aliphatic ester solvent; and the 2-nitro-2′-carboxy-diphenylsulfide compound is suitably prepared by reacting a nitrobenzene compound with a thiosalicylic acid compound in a mixture of a lower aliphatic alcohol and water.

  通过在酸性催化剂的存在下，将2-氨基-2'-羧基二苯硫醚化合物进行脱水缩合反应，可以适当地制备二苯并噻吩类化合物；2-氨基-2'-羧基二苯硫醚化合物可以通过在较低的脂肪酯溶剂中还原2-硝基-2'-羧基二苯硫醚化合物来适当地制备；而2-硝基-2'-羧基二苯硫醚化合物可以通过在较低脂肪醇和水的混合物中，将硝基苯化合物与硫代水杨酸类化合物反应来适当地制备。
• Process for preparing dibenzothiazepine derivatives
  申请人：Harada Katsumasa

  公开号：US20060173178A1

  公开（公告）日：2006-08-03

  A process for preparing a dibenzothiazepine derivative such as dibenzo[b,f][1,4]thiazepin-11-one employable as a starting material for the preparation of 11-[4-(2-(2-hydroxyethoxy)ethyl)]-1-piperadinyldibenzothiazepine derivative which is known to be effective as an antipsychotic pharmaceutical, has the steps of reacting a nitrobenzene derivative with a thiosalicylic acid derivative, reducing the obtained 2-nitro-2′-carboxy-diphenylsulfide derivative, and subjecting the obtained 2-amino-2′-carboxy-diphenylsulfide derivative to dehydration-condensation reaction.

  一种制备二苯并噻吩衍生物的方法，例如二苯并[b，f][1,4]噻吩-11-酮，可用作制备11-[4-(2-(2-羟乙氧基)乙基)]-1-哌嗪基二苯并噻吩衍生物的起始物质，该衍生物已知对抗精神病药物有效，包括以下步骤：将硝基苯衍生物与硫氧化水杨酸衍生物反应，还原所得的2-硝基-2'-羧基二苯基硫醚衍生物，并将所得的2-氨基-2'-羧基二苯基硫醚衍生物进行脱水缩合反应。
• Carbon-11 and fluorine-18 labeled radioligands for positron emission tomography (PET) imaging for the brain serotonin transporters
  申请人：Huang Yiyun

  公开号：US20110097274A1

  公开（公告）日：2011-04-28

  This invention provides a compound having the structure: This invention also provides for related compounds and pharmaceutical compositions. This invention further provides for a compound that can be used for non-invasive method for positron emission tomography (PET) imaging of serotonin transporter sites in mammals comprising labeling serotonin transporter sites (SERT) with an image-generating amount of the radiolabeled compound disclosed herein and measuring spatial distribution of the compound in the mammal by PET so as to thereby image the serotonin transporter sites.

  这项发明提供了一种具有以下结构的化合物：此外，本发明还提供了相关的化合物和制药组合物。此外，本发明还提供了一种化合物，可用于非侵入性的正电子发射断层扫描（PET）成像方法，用于哺乳动物中的血清素转运体位点成像，包括使用本文所述的放射性标记化合物标记血清素转运体位点（SERT），并通过PET测量哺乳动物中化合物的空间分布，从而成像血清素转运体位点。
• PROCESS FOR PRODUCING DIBENZOTHIAZEPINE DERIVATIVES
  申请人：Ube Industries, Ltd.

  公开号：EP1201663A1

  公开（公告）日：2002-05-02

  A process for preparing a dibenzothiazepine derivative such as dibenzo[b,f] [1,4]thiazepin-11-one employable as a starting material for the preparation of 11-[4-(2-(2-hydroxyethoxy)ethyl)]-1-piperadinyldiberizothiazepine derivative which is known to be effective as an antipsychotic pharmaceutical, has the steps of reacting a nitrobenzene derivative with a thiosalicylic acid derivative, reducing the obtained 2-nitro-2'-carboxy-diphenylsulfide derivative, and subjecting the obtained 2-amino-2'-carboxy-diphenylsulfide derivative to dehydration-condensation reaction.

  一种制备二苯并硫氮杂卓衍生物如二苯并[b,f][1,4]硫氮杂卓-11-酮的工艺，可用作制备 11-[4-(2-(2-羟基乙氧基)乙基)]-1-哌啶基二苯并硫氮杂卓衍生物的起始原料，该衍生物已知可有效地用作抗精神病药物、其步骤包括使硝基苯衍生物与硫代水杨酸衍生物反应，还原得到的 2-硝基-2'-羧基-二苯硫醚衍生物，并使得到的 2-氨基-2'-羧基-二苯硫醚衍生物进行脱水缩合反应。
• Jarkas, Nachwa; McConathy, Jonathan; Ely, Timothy, Journal of labelled compounds and radiopharmaceuticals, 2001, vol. 44, p. S204 - S206
  作者：Jarkas, Nachwa、McConathy, Jonathan、Ely, Timothy、Kilts, Clinton D.、Votaw, John、Goodman, Mark M.

  DOI：——

  日期：——