6-fluoro-benzo[b]thiophene-2-sulfonyl chloride | 205055-11-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 6-fluoro-benzo[b]thiophene-2-sulfonyl chloride
• 英文别名: 6-Fluorobenzo[b]thiophene-2-sulfonyl chloride；6-fluoro-1-benzothiophene-2-sulfonyl chloride
• CAS: 205055-11-4
• 化学式: C₈H₄ClFO₂S₂
• 分子量: 250.702
• InChiKey: KVJPMFBFSAZRQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-fluoro-benzo[b]thiophene-2-sulfonyl chloride 、 (3S)-1-[3-(6-fluoro-1,2-benzoxazol-3-yl)propyl]pyrrolidine-3-amine hydrochloride 在 4-二甲氨基吡啶 、 caesium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 (S)-6-fluoro-N-(1-(3-(6-fluorobenzo[d]isoxazol-3-yl)propyl)pyrrolidin-3-yl)benzo[b]thiophene-2-sulfonamide
  参考文献：
  名称：

  Multifunctional 6-fluoro-3-[3-(pyrrolidin-1-yl)propyl]-1,2-benzoxazoles targeting behavioral and psychological symptoms of dementia (BPSD)

  摘要：

  Patients suffering from dementia experience cognitive deficits and 90% of them show non-cognitive behavioral and psychological symptoms of dementia (BPSD). The spectrum of BPSD includes agitation, depression, anxiety and psychosis. Antipsychotics, e.g. quetiapine, have been commonly used off-label to control the burdensome symptoms, though they cause serious side effects and further cognitive impairment. Therefore, the development of targeted therapy for BPSD, suitable for elderly patients, remains relevant.A multitarget-directed ligand, acting on serotonin 5-HT2A and dopamine D-2 receptors (R) and thus exerting anti-aggressive and antipsychotic activity, as well as on 5-HT(6)Rs and 5-HT(7)Rs ( potential procognitive, antidepressant and anxiolytic activity), poses a promising strategy for the treatment of BPSD. Antitargeting muscarinic M3R and hERG channel is expected to reduce the risk of side effects. We obtained a series of stereoisomeric compounds by combining 6-fluoro-1,2-benzoxazole moiety and arylsulfonamide fragment through pyrrolidin-1-yl-propyl linker.N-[(3R)-1-[3-(6-fluoro-1,2-benzoxazol-3-yl)propyl]pyrrolidin-3-yl]-1-benzothiophene-2-sulfonamide showed a substantial affinity for the targets of interest (pK(i) = 8.32-9.35) and no significant interaction with the antitargets. Functional studies revealed its antagonist efficacy (pK(B) = 7.41-9.03). The lead compound showed a promising profile of antipsychotic-like activity in amphetamine- and MK-801-induced hyperlocomotion (MED = 2.5 mg/kg), antidepressant-like, as well as anxiolytic-like activity in mice (MED = 0.312 and 1.25 mg/kg in the forced swim and four-plate tests, respectively). Notably, the novel compound didn't affect spontaneous locomotor activity, nor induced catalepsy or memory deficits (step-through passive avoidance test) in therapeutically relevant doses, which proved its benign safety profile. The overall pharmacological characteristics of the lead compound outperformed the reference drug quetiapine, making it a promising option for evaluation in the treatment of BPSD. (c) 2020 The Authors. Published by Elsevier Masson SAS. This is an open access article under the CC BY license (http://creativecommons.org/licenses/by/4.0/).

  DOI：

  10.1016/j.ejmech.2020.112149
• 作为产物：
  描述：

  3-氟苯硫酚 生成 6-fluoro-benzo[b]thiophene-2-sulfonyl chloride
  参考文献：
  名称：

  Sulfonic acid sulfonylamino n-(heteroaralkyl)-azaheterocyclylamide compounds

  摘要：

  本文中的化合物具有有用的药理活性，因此被纳入药物组合物中，并用于治疗患有某些医学疾病的患者。更具体地说，它们是凝血因子Xa活性的抑制剂。本发明涉及具有I式化合物的化合物、含有I式化合物的组合物，以及它们的用途，用于治疗患有或受到生理状况影响的患者，这些生理状况可以通过给予凝血因子Xa活性抑制剂来改善。

  公开号：

  US06281227B1
• 作为试剂：
  描述：

  3-(S)-amino-1-(furo[3,2-b]pyridin-2-ylmethyl)-pyrrolidin-2-one hydrochloride 以 6-fluoro-benzo[b]thiophene-2-sulfonyl chloride 为溶剂， 生成 6-Fluoro-benzo[b]thiophene-2-sulfonic acid (1-furo[3,2-b]pyridin-2-ylmethyl-2-oxopyrrolidin3-(S)-yl)-amide
  参考文献：
  名称：

  Sulfonic acid sulfonylamino n-(heteroaralkyl)-azaheterocyclylamide compounds

  摘要：

  本文中的化合物具有有用的药理活性，因此被纳入药物组合物中，并用于治疗患有某些医学疾病的患者。更具体地说，它们是凝血因子Xa活性的抑制剂。本发明涉及具有I式化合物的化合物、含有I式化合物的组合物，以及它们的用途，用于治疗患有或受到生理状况影响的患者，这些生理状况可以通过给予凝血因子Xa活性抑制剂来改善。

  公开号：

  US06281227B1

文献信息

• Substituted sulfonic acid
  申请人：Rhone-Poulenc Rorer Pharmaceuticals Inc.

  公开号：US06034093A1

  公开（公告）日：2000-03-07

  The compounds of formula I exhibit useful pharmacological activity and accordingly are incorporated into pharmaceutical compositions and used in the treatment of patients suffering from certain medical disorders. More specifically, they are inhibitors of the activity of Factor Xa. The present invention is directed to compounds of formula I, compositions containing compounds of formula I, and their use, which are for treating a patient suffering from, or subject to, physiological condition which can be ameliorated by the administration of an inhibitor of the activity of Factor Xa.

  公式I的化合物表现出有用的药理活性，因此被纳入药物组合物中，并用于治疗患有某些医学疾病的患者。更具体地说，它们是凝血因子Xa活性的抑制剂。本发明涉及公式I的化合物、含有公式I化合物的组合物，以及它们的用途，用于治疗患有或受到可通过给予凝血因子Xa活性抑制剂而得到改善的生理状况的患者。
• SULPHONAMIDE DERIVATIVES OF ALICYCLIC AMINES FOR THE TREATMENT OF CENTRAL NERVOUS SYSTEM DISEASES
  申请人：Kolaczkowski Marcin

  公开号：US20140135310A1

  公开（公告）日：2014-05-15

  Sulphonamide derivatives of alicyclic amines of formula (I), wherein A represents naphthyl or 9- or 10-membered bicyclic group, consisting of benzene ring fused with 5- or 6-membered heterocyclic ring; D represents phenyl, naphthyl, 5-membered aromatic heterocyclic group, bicyclic group consisting of a ring selected from benzene and pyridine, fused with aromatic or non-aromatic 5-membered heterocyclic ring; p, r independently represent 0 or 1; x, z independently represent 1 or 2; n is 2 or 3; and enancjomers, pharmaceutically acceptable salts and solvates thereof. The compounds may be useful for the treatment and/or prevention of the central nervous system disorders.

  环脂肪胺的磺胺衍生物的化学式(I)，其中A代表萘基或9-或10-成员双环基团，由苯环与5-或6-成员杂环环融合而成；D代表苯基，萘基，5-成员芳香杂环基团，由苯环和吡啶中选择的环融合而成，与芳香或非芳香5-成员杂环环融合；p，r独立地代表0或1；x，z独立地代表1或2；n为2或3；其对映体，药学上可接受的盐及溶剂化合物。这些化合物可能对中枢神经系统疾病的治疗和/或预防有用。
• Sulfonic acid or sulfonylamino N-(heteroaralkyl)-azaheterocyclylamide compounds
  申请人：——

  公开号：US20020013310A1

  公开（公告）日：2002-01-31

  The compounds of formula I herein exhibit useful pharmacological activity and accordingly are incorporated into pharmaceutical compositions and used in the treatment of patients suffering from certain medical disorders. More specifically, they are inhibitors of the activity of Factor Xa. The present invention is directed to compounds of formula I, compositions containing compounds of formula I, and their use, for treating a patient suffering from, or subject to, a physiological condition which can be ameliorated by the administration of an inhibitor of the activity of Factor Xa.

  本文中的I式化合物表现出有用的药理活性，因此被纳入制药组合物中，并用于治疗患有某些医学疾病的患者。更具体地说，它们是Factor Xa活性的抑制剂。本发明涉及I式化合物、含有I式化合物的组合物以及它们的使用，用于治疗患有或受到生理状况影响的患者，这些状况可以通过给予Factor Xa活性抑制剂的治疗得到改善。
• Multifunctional Arylsulfone and Arylsulfonamide-Based Ligands with Prominent Mood-Modulating Activity and Benign Safety Profile, Targeting Neuropsychiatric Symptoms of Dementia
  作者：Monika Marcinkowska、Adam Bucki、Joanna Sniecikowska、Agnieszka Zagórska、Nikola Fajkis-Zajączkowska、Agata Siwek、Monika Gluch-Lutwin、Paweł Żmudzki、Magdalena Jastrzebska-Wiesek、Anna Partyka、Anna Wesołowska、Michał Abram、Katarzyna Przejczowska-Pomierny、Agnieszka Cios、Elżbieta Wyska、Kamil Mika、Magdalena Kotańska、Paweł Mierzejewski、Marcin Kolaczkowski

  DOI：10.1021/acs.jmedchem.1c00497

  日期：2021.9.9
• SUBSTITUTED SULFONIC ACID N- (AMINOIMINOMETHYL)PHENYLALKYL]-AZAHETEROCYCLAMIDE COMPOUNDS
  申请人：RHONE-POULENC RORER PHARMACEUTICALS, INC.

  公开号：EP0894088A1

  公开（公告）日：1999-02-03