3-氨基-4-氯苯硫醇 | 70502-87-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯硫酚类
• 中文名称: 3-氨基-4-氯苯硫醇
• 英文名称: 3-amino-4-chlorobenzenethiol
• CAS: 70502-87-3
• 化学式: C₆H₆ClNS
• 分子量: 159.639
• InChiKey: GWYXGAVKUBLXOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  27
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-氨基-4-氯苯硫醇 在 盐酸 、 aluminum (III) chloride 、 正丁基锂 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 甲苯 为溶剂， 反应 7.0h， 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(ll) chloride 作用下， 以 水 为溶剂， 反应 4.0h， 生成 3-氨基-4-氯苯硫醇
  参考文献：
  名称：

  Development of an automated, GMP compliant FASTlab™ radiosynthesis of [¹⁸ F]GE-179 for the clinical study of activated NMDA receptors

  摘要：

  N-(2-氯-5-(S-2-[18F]氟乙基)噻苄基)-N'-(3-硫甲基苯基)-N'-甲基胍（[18F]GE-179）已被确定为一种有前景的正电子发射断层扫描（PET）配体，用于N-甲基-D-天冬氨酸（NMDA）受体的通道内苯环神经磷（PCP）结合位点。[18F]GE-179的放射合成仅在低放射活度水平下进行。然而，为了进行临床研究，需要制造出符合GMP标准的高放射活度产品。我们描述了一种使用GE FASTlab™放射合成平台结合HPLC纯化的工艺开发。放射合成是一个两步过程，涉及对乙烯二托烯磺酸酯11的核取代氟化，随后对去质子化的硫醇前体，N-(2-氯-5-噻苄醇)-N'-(3-硫甲基苯基)-N'-甲基胍8进行烷基化。粗产品通过半制备HPLC进行纯化，得到的制剂产品放射活度产率（AY）为7 ± 2%（n = 15），总合成时间为120分钟。放射性浓度（RAC）和放射化学纯度（RCP）分别为328 ± 77 MBq/mL和96.5 ± 1%，总化学含量为2 ± 1 μg。最终制剂体积为14 mL。之前描述的[18F]GE-179的放射合成成功地进行修改，从而在FASTlab™上提供了一种工艺，使得可以从高起始放射活度（最多80 GBq）制造出GMP品质的产品，最终产品适合临床使用。

  DOI：

  10.1002/jlcr.3831

文献信息

• Development of an automated, GMP compliant FASTlab™ radiosynthesis of [¹⁸ F]GE-179 for the clinical study of activated NMDA receptors
  作者：Imtiaz Khan、Tom Christian Berg、Jane Brown、Rajiv Bhalla、Anthony Wilson、Andrew Black、Graeme McRobbie、James Nairne、Andreas Olsson、William Trigg

  DOI：10.1002/jlcr.3831

  日期：2020.4

  N-(2-chloro-5-(S-2-[18F]fluoroethyl)thiophenyl)-N'-(3-thiomethylphenyl)-N'-methylguanidine, ([18F]GE-179), has been identified as a promising positron emission tomography (PET) ligand for the intra-channel phencyclidine (PCP) binding site of the N-methyl-D-aspartate (NMDA) receptor. The radiosynthesis of [18F]GE-179 has only been performed at low radioactivity levels. However, the manufacture of a GMP compliant product at high radioactivity levels was required for clinical studies. We describe the development of a process using the GE FASTlab™ radiosynthesis platform coupled with HPLC purification. The radiosynthesis is a two-step process, involving the nucleophilic fluorination of ethylene ditosylate, 11, followed by alkylation to the deprotonated thiol precursor, N-(2-chloro-5-thiophenol)-N'-(3-thiomethylphenyl)-N'-methyl guanidine, 8. The crude product was purified by semi-preparative HPLC to give the formulated product in an activity yield (AY) of 7 ± 2% (n = 15) with a total synthesis time of 120 minutes. The radioactive concentration (RAC) and radiochemical purity (RCP) were 328 ± 77 MBq/mL and 96.5 ± 1% respectively and the total chemical content was 2 ± 1 μg. The final formulation volume was 14 mL. The previously described radiosynthesis of [18F]GE-179 was successfully modified to deliver an process on the FASTlab™ that allows the manufacture of a GMP quality product from high starting radioactivitity (up to 80 GBq) and delivers a product suitable for clinical use.

  N-(2-氯-5-(S-2-[18F]氟乙基)噻苄基)-N'-(3-硫甲基苯基)-N'-甲基胍（[18F]GE-179）已被确定为一种有前景的正电子发射断层扫描（PET）配体，用于N-甲基-D-天冬氨酸（NMDA）受体的通道内苯环神经磷（PCP）结合位点。[18F]GE-179的放射合成仅在低放射活度水平下进行。然而，为了进行临床研究，需要制造出符合GMP标准的高放射活度产品。我们描述了一种使用GE FASTlab™放射合成平台结合HPLC纯化的工艺开发。放射合成是一个两步过程，涉及对乙烯二托烯磺酸酯11的核取代氟化，随后对去质子化的硫醇前体，N-(2-氯-5-噻苄醇)-N'-(3-硫甲基苯基)-N'-甲基胍8进行烷基化。粗产品通过半制备HPLC进行纯化，得到的制剂产品放射活度产率（AY）为7 ± 2%（n = 15），总合成时间为120分钟。放射性浓度（RAC）和放射化学纯度（RCP）分别为328 ± 77 MBq/mL和96.5 ± 1%，总化学含量为2 ± 1 μg。最终制剂体积为14 mL。之前描述的[18F]GE-179的放射合成成功地进行修改，从而在FASTlab™上提供了一种工艺，使得可以从高起始放射活度（最多80 GBq）制造出GMP品质的产品，最终产品适合临床使用。
• 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。
• [EN] ALKYLATION METHOD<br/>[FR] PROCÉDÉ D'ALKYLATION
  申请人：GE HEALTHCARE LTD

  公开号：WO2017186969A1

  公开（公告）日：2017-11-02

  The present invention relates to a method of radiochemical synthesis which is useful in the synthesis of a positron emission tomography (PET) tracer.

  本发明涉及一种放射化学合成方法，该方法在正电子发射断层扫描（PET）示踪剂合成中有用。
• Color photographic light-sensitive element
  申请人：Fuji Photo Film Co., Ltd.

  公开号：US04199361A1

  公开（公告）日：1980-04-22

  A color photographic light-sensitive element comprising a support having thereon a silver halide emulsion layer containing therein a 3-anilino-5-pyrazolone magenta color-forming coupler represented by the following general formula (I): ##STR1## wherein R represents an aliphatic hydrocarbon group having up to about 35 carbon atoms, a heterocyclic group having up to about 22 carbon atoms or an aromatic group having up to about 22 carbon atoms; X represents a halogen atom or an alkoxy group having up to about 22 carbon atoms; Z represents a hydrogen atom or a coupling off group; and Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4 and Y.sub.5, which may be the same or different, each represents a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 5 carbon atoms, a trifluoromethyl group, an alkoxy group having 1 to 5 carbon atoms, an acylamino group having 1 to 30 carbon atoms, an alkylsulfonyl group having 2 to 30 carbon atoms or a sulfonamido group having 1 to 30 carbon atoms and the RS group is present at the 4- or 5-position of the anilino group. The magenta color-forming coupler prevents yellow staining at the unexposed area after color development processing particularly arising due to irradiation of light.

  一种彩色摄影感光元件，包括具有银卤素乳剂层的支撑体，所述银卤素乳剂层中含有下式（I）所表示的3-苯胺基-5-吡唑酮品红色成色偶合剂： 其中，R代表具有最多约35个碳原子的脂肪烃基，最多约22个碳原子的杂环基或最多约22个碳原子的芳香基；X代表一个卤素原子或最多约22个碳原子的烷氧基；Z代表氢原子或偶合离子基；Y1、Y2、Y3、Y4和Y5，它们可以相同也可以不同，每个代表氢原子、卤素原子、氰基、具有1至5个碳原子的烷基、三氟甲基、具有1至5个碳原子的烷氧基、具有1至30个碳原子的酰胺基、具有2至30个碳原子的烷基磺酰基或具有1至30个碳原子的磺酰胺基，且RS基位于苯胺基的4-或5-位。该品红色成色偶合剂可防止因光照引起的彩色显影处理后未曝光区域出现黄色污染。
• METHOD FOR PRODUCING BIARYL COMPOUND
  申请人：Sato Koichi

  公开号：US20100087680A1

  公开（公告）日：2010-04-08

  A method for producing a biaryl compound, comprising reacting an aromatic organic compound with at least one compound selected from the group consisting of aromatic organoboron compounds and boroxine compounds, in the presence of a zero-valent nickel catalyst, phosphine ligand and base.

  一种制备双芳基化合物的方法，包括在零价镍催化剂、膦配体和碱的存在下，将芳香有机化合物与选自芳香基有机硼化合物和硼氧化物化合物组的至少一种化合物反应。

表征谱图