6-溴-1,3-二氢-2H-咪唑并[4,5-b]吡啶-2-硫酮 | 93752-20-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 中文名称: 6-溴-1,3-二氢-2H-咪唑并[4,5-b]吡啶-2-硫酮
• 英文名称: 6-bromo-3H-imidazo[4,5-b]pyridine-2-thiol
• 英文别名: 6-bromo-1,3-dihydro-2H-imidazo[4,5-b]pyridine-2-thione；6-bromo-1,3-dihydroimidazo[4,5-b]pyridine-2-thione
• CAS: 93752-20-6
• 化学式: C₆H₄BrN₃S
• mdl: MFCD03547056
• 分子量: 230.088
• InChiKey: AOLQXGYCKFKIPQ-UHFFFAOYSA-N

物化性质

• 溶解度：
  34.4 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  69
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  6-溴-1,3-二氢-2H-咪唑并[4,5-b]吡啶-2-硫酮 在 sodium hydroxide 、 sodium acetate 、 乙酸酐 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 2-benzylidene-7-bromo-thiazolo[2',3':2,3]imidazo[4,5-b]pyridin-3-one
  参考文献：
  名称：

  Synthesis and Antiproliferative Activity in vitro of New Tricyclic 2-Thioxo-1 H ,3 H -imidazo[4,5-b]pyridine Derivatives

  摘要：

  A series of 2-arylidenethiazolo[2',3':2,3]imidazo[4,5-b]pyridine-2-yl-3-ones were prepared by a reaction of 6-bromo- (4) or 3H-imidazo[4,5-b]pyridin-2-ylthioglycolic acid (3) with appropriate aromatic aldehydes. All new compounds were examined for their antiproliferative activity in vitro against cells of human cancer cell lines, using SRB technique. Preliminary screening data indicated that three of the tested compounds revealed cytotoxic activity.

  DOI：

  10.1080/10426500600892594
• 作为产物：
  描述：

  6-溴-4氢-咪唑并[4,5-B]吡啶 在 sulfur 作用下， 反应 1.0h， 以99%的产率得到6-溴-1,3-二氢-2H-咪唑并[4,5-b]吡啶-2-硫酮
  参考文献：
  名称：

  Thionation of imidazopyridines

  摘要：

  DOI：

  10.1007/bf00475602

文献信息

• Imidazopyridine- and Purine-Thioacetamide Derivatives: Potent Inhibitors of Nucleotide Pyrophosphatase/Phosphodiesterase 1 (NPP1)
  作者：Lei Chang、Sang-Yong Lee、Piotr Leonczak、Jef Rozenski、Steven De Jonghe、Theodor Hanck、Christa E. Müller、Piet Herdewijn

  DOI：10.1021/jm501434y

  日期：2014.12.11

  Nucleotide pyrophosphatase/phosphodiesterase 1 (NPP1) belongs to the family of ecto-nucleotidases, which control extracellular nucleotide, nucleoside, and (di)phosphate levels. To study the (patho)physiological roles of NPP1 potent and selective inhibitors with drug-like properties are required. Therefore, a compound library was screened for NPP1 inhibitors using a colorimetric assay with p-nitrophenyl

  核苷酸焦磷酸酶/磷酸二酯酶1（NPP1）属于胞外核苷酸酶家族，可控制细胞外核苷酸，核苷和（di）磷酸盐的水平。为了研究具有药物样特性的NPP1强效和选择性抑制剂的（病理）生理作用。因此，使用比色测定法以对硝基苯基5'-胸苷单磷酸酯（p -Nph-5'-TMP）作为人工底物，筛选化合物库中的NPP1抑制剂。这导致发现2-（3 H-咪唑并[4,5 - b ]吡啶-2-基硫基）-N-（3,4-二甲氧基苯基）乙酰胺（5a）为具有K i的命中化合物。值为217 nM。随后的结构-活性关系研究导致了嘌呤和咪唑并[4,5- b ]吡啶类似物的开发，用p -Nph-5'-进行测定具有高抑制力（K i值分别为5.00 nM和29.6 nM）。以TMP为底物。出乎意料的是，与ATP作为底物相比，测试时这些化合物的效力明显较低，K i值在低微摩尔范围内。对原型抑制剂的抑制机理进行了研究，发现该抑制剂与两种底物都具有竞争性。
• [EN] SUBSTITUTED BENZIMIDAZOLE CARBOXAMIDES AND THEIR USE IN THE TREATMENT OF MEDICAL DISORDERS<br/>[FR] BENZIMIDAZOLE CARBOXAMIDES SUBSTITUÉS ET LEUR UTILISATION DANS LE TRAITEMENT DE TROUBLES MÉDICAUX
  申请人：BIAL BIOTECH INVEST INC

  公开号：WO2021055591A1

  公开（公告）日：2021-03-25

  The invention provides substituted benzimidazole carboxamides and related compounds, compositions containing such compounds, medical kits, and methods for using such compounds and compositions to treat a medical disorder, e.g., cancer, lysosomal storage disorder, neurodegenerative disorder, inflammatory disorder, in a patient.

  这项发明提供了替代苯并咪唑羧酰胺及相关化合物，含有这些化合物的组合物，医疗工具包，以及使用这些化合物和组合物治疗患者的医疗疾病的方法，例如癌症、溶酶体贮积症、神经退行性疾病、炎症性疾病。
• Pharmaceutical compositions and methods for use
  申请人：——

  公开号：US20020058652A1

  公开（公告）日：2002-05-16

  The present invention relates to aryl olefinic azacyclic compounds and aryl acetylenic azacyclic compounds, including pyridyl olefinic cycloalkylamines and pyridyl acetylenic cycloalkylamines. The present invention also relates to prodrug derivatives of the compounds of the present invention.

  本发明涉及芳基烯丙基氮杂环化合物和芳基炔丙基氮杂环化合物，包括吡啶基烯丙基环烷基胺和吡啶基炔丙基环烷基胺。本发明还涉及本发明化合物的药物前体衍生物。
• [EN] PHARMACEUTICAL COMPOSITIONS AND METHODS FOR USE<br/>[FR] COMPOSITIONS PHARMACEUTIQUES ET METHODES D'UTILISATION
  申请人：TARGACEPT INC

  公开号：WO2000075110A1

  公开（公告）日：2000-12-14

  Pharmaceutical compositions incorporate aryl substituted olefinic amine compounds. Representative compounds are (2S)-(4E)-N-methyl-5-[3-(5-isopropoxy-1-oxopyridin)yl)]-4-penten-2-amine, (3E)-N-methyl-4-(3-(1-oxopyridin)yl)-3-buten-1-amine, (4E)-N-methyl-5-(3-(1-oxopyridin)yl)-4-penten-2-amine, (4E)-N-methyl-5-(3-(5-((carboxymethyl)oxy)pyridin)yl)-4-penten-2-amine, (3E)-N-methyl-4-[3-(5-nitro-6-aminopyridin)yl]-3-buten-1-amine, (3E)-N-methyl-4-[3-(5-(N-benzylcarboxamido)pyridin)yl]-3-buten-1-amine(4E)-N-methyl-5-[5-(2-aminopyrimidin)yl]-4-penten-2-amine, (4E)-N-methyl-5-(3-(5-aminopyridin)yl)-4-penten-2-amine (3E)-N-methyl-4-(3-(5-isobutoxypyridin)yl)-3-buten-1-amine, (3E)-N-methyl-4-(3-(5-ethylthiopyridin)yl)-3-buten-1-amine, (4E)-N-methyl-5-(3-(5-trifluoromethylpyridin)yl)-4-penten-2-amine, (4E)-5-(3-(5-isopropoxypyridin)yl)-4-penten-2-amine, and (4E)-5-(3-(5-isopropoxypyridin)yl)-4-penten-2-amine.

  制药组合物包括芳基取代烯丙胺化合物。代表性化合物有(2S)-(4E)-N-甲基-5-[3-(5-异丙氧基-1-氧代吡啶)基)]-4-戊烯-2-胺，(3E)-N-甲基-4-(3-(1-氧代吡啶)基)-3-丁烯-1-胺，(4E)-N-甲基-5-(3-(1-氧代吡啶)基)-4-戊烯-2-胺，(4E)-N-甲基-5-(3-(5-((羧甲基)氧基)吡啶)基)-4-戊烯-2-胺，(3E)-N-甲基-4-[3-(5-硝基-6-氨基吡啶)基]-3-丁烯-1-胺，(3E)-N-甲基-4-[3-(5-(N-苯甲酰基)吡啶)基]-3-丁烯-1-胺，(4E)-N-甲基-5-[5-(2-氨基嘧啶)基]-4-戊烯-2-胺，(4E)-N-甲基-5-(3-(5-氨基吡啶)基)-4-戊烯-2-胺，(3E)-N-甲基-4-(3-(5-异丁氧基吡啶)基)-3-丁烯-1-胺，(3E)-N-甲基-4-(3-(5-乙硫基吡啶)基)-3-丁烯-1-胺，(4E)-N-甲基-5-(3-(5-三氟甲基吡啶)基)-4-戊烯-2-胺，(4E)-5-(3-(5-异丙氧基吡啶)基)-4-戊烯-2-胺，以及(4E)-5-(3-(5-异丙氧基吡啶)基)-4-戊烯-2-胺。
• Hydroxybenzoate salts of metanicotine compounds
  申请人：Munoz A. Julio

  公开号：US20060122237A1

  公开（公告）日：2006-06-08

  Patients susceptible to or suffering from conditions and disorders, such as central nervous system disorders, are treated by administering to a patient in need thereof compositions that are hydroxybenzoate salts of E-metanicotine-type compounds. The formation of hydroxybenzoate salts of the E-metanicotine compounds is also useful in purifying the E-metanicotine compounds, as the hydroxybenzoate salts tend to crystallize out, leaving impurities such as Z-metanicotine compounds, and compounds where the double bond has migrated, in solution. If desired, the hydroxybenzoate salts can be converted to either the free base (the E-metanicotine) or to another pharmaceutically acceptable salt form.

  易感或患有中枢神经系统疾病等状况的患者，通过向需要治疗的患者施用氢氧基苯酸盐型的E-甲基烟碱类化合物来进行治疗。形成E-甲基烟碱化合物的氢氧基苯酸盐也可用于纯化E-甲基烟碱化合物，因为氢氧基苯酸盐倾向于结晶出来，留下杂质，如Z-甲基烟碱化合物和双键迁移的化合物在溶液中。如果需要，氢氧基苯酸盐可以转化为自由基（E-甲基烟碱）或其他药学上可接受的盐形式。