6-甲氧基-1-苯并噻吩-2-甲腈 | 92014-05-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 中文名称: 6-甲氧基-1-苯并噻吩-2-甲腈
• 英文名称: 2-cyano-6-methoxybenzothiophene
• 英文别名: 6-methoxy-2-cyanobenzothiophene；6-methoxy-1-benzothiophene-2-carbonitrile；6-methoxybenzo[b]thiophene-2-carbonitrile；2-cyano-6-methoxybenzothiophene
• CAS: 92014-05-6
• 化学式: C₁₀H₇NOS
• 分子量: 189.238
• InChiKey: LLMUULCPDPIINA-UHFFFAOYSA-N

物化性质

• 熔点：
  83-84 °C
• 沸点：
  352.0±22.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  61.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-甲氧基-1-苯并噻吩-2-甲腈 在 吡啶盐酸盐 作用下， 以 水 、 乙腈 为溶剂， 生成 D-benzothiophenylluciferin
  参考文献：
  名称：

  萤火虫萤光素的新型杂环类似物

  摘要：

  合成了五个新颖的萤火虫荧光素类似物，其中天然底物的苯​​并噻唑环系统被苯并咪唑，苯并呋喃，苯并噻吩，苯并恶唑和吲哚代替。用重组Photinus pyralis评估化合物的荧光，生物发光和动力学性质野生型荧光素酶。除吲哚外，所有含有杂环取代基的底物均使用荧光素酶产生易于测量的闪光。与萤光素相比，在具有最佳pH和达到最大强度的时间不同的反应中，强度范围为0.3％至4.4％。杂原子的变化影响了荧光和生物发光发射光谱，分别显示了479-528和518-574 nm的最大值。虽然这组结构相似的底物类似物在光谱和生物发光特性方面存在一些有趣的趋势，但最重要的发现与含苯并噻吩的化合物有关。这种合成的底物产生缓慢的衰变辉光动力学，使荧光素酶的总基于光的比活性相对于荧光素值增加了4倍以上。此外，在6.2-9.4的pH范围内，最大发射为523 nm，与天然底物相比，蓝移异常37纳米。苯并噻吩荧光素的非凡的生物

  DOI：

  10.1021/bi301411d
• 作为产物：
  描述：

  dimethylthiocarbamic acid O-(2-formyl-5-methoxyphenyl) ester 在 水 、 potassium carbonate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 6-甲氧基-1-苯并噻吩-2-甲腈
  参考文献：
  名称：

  萤火虫萤光素的新型杂环类似物

  摘要：

  合成了五个新颖的萤火虫荧光素类似物，其中天然底物的苯​​并噻唑环系统被苯并咪唑，苯并呋喃，苯并噻吩，苯并恶唑和吲哚代替。用重组Photinus pyralis评估化合物的荧光，生物发光和动力学性质野生型荧光素酶。除吲哚外，所有含有杂环取代基的底物均使用荧光素酶产生易于测量的闪光。与萤光素相比，在具有最佳pH和达到最大强度的时间不同的反应中，强度范围为0.3％至4.4％。杂原子的变化影响了荧光和生物发光发射光谱，分别显示了479-528和518-574 nm的最大值。虽然这组结构相似的底物类似物在光谱和生物发光特性方面存在一些有趣的趋势，但最重要的发现与含苯并噻吩的化合物有关。这种合成的底物产生缓慢的衰变辉光动力学，使荧光素酶的总基于光的比活性相对于荧光素值增加了4倍以上。此外，在6.2-9.4的pH范围内，最大发射为523 nm，与天然底物相比，蓝移异常37纳米。苯并噻吩荧光素的非凡的生物

  DOI：

  10.1021/bi301411d

文献信息

• [EN] 3-ARYLOXY/ THIO-2, 3-SUBSTITUTED PROPANAMINES AND THEIR USE IN INHIBITING SEROTONIN AND NOREPINEPHRINE REUPTAKE<br/>[FR] 3-ARYLOXY/THIO-2, 3-SUBSTITUE PROPANAMINES ET LEUR UTILISATION POUR INHIBER LE RECAPTAGE DE LA SEROTONINE ET DE LA NOREPINEPHRINE
  申请人：LILLY CO ELI

  公开号：WO2004043903A1

  公开（公告）日：2004-05-27

  There is provided a compound of formula (I) wherein A is selected from -O- and -S-; X is selected from phenyl optionally substituted with up to 5 substituents each independently selected from halo, C1-C4 alkyl and C1-C4 alkoxy, thienyl optionally substituted with up to 3 substituents each independently selected from halo and C1-C4 alkyl, and C2-C8 alkyl, C2-C8 alkenyl, C3-C8 cycloalkyl and C4-C8 cycloalkylalkyl, each of which may be optionally substituted with up to 3 substituents each independently selected from halo, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkyl-S(O)n- where n is 0, 1 or 2, -CF3, -CN and -CONH2; Y is selected from phenyl, naphthyl, dihydrobenzothienyl, benzothiazolyl, benzoisothiazolyl, quinolyl, isoquinolyl, naphthyridyl, thienopyridyl, indanyl, 1,3-benzodioxolyl, benzothienyl, indolyl and benzofuranyl, each of which may be optionally substituted with up to 4 or, where possible, up to 5 substituents each independently selected from halo, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkyl-S(O)n- where n is 0, 1 or 2, nitro, acetyl, -CF3, -SCF3 and cyano; and when Y is indolyl it may be substituted or further substituted by an N-substituent selected from C1-C4 alkyl; Z is selected from OR3 or F, wherein R3 is selected from H, C1-C6 alkyl and phenyl C1-C6 alkyl; R1 and R2 are each independently H or C1-C4 alkyl; and pharmaceutically acceptable salts thereofwith the proviso that when Y is optionally substituted phenyl or optionally substituted 1,3-benzodioxolyl and Z is OR3 and X is optionally substituted phenyl then A is -S-.

  提供一种化合物，其化学式为（I），其中A从-O-和-S-中选择；X从苯基选项地取代，每个取代基可独立地从卤素、C1-C4烷基和C1-C4烷氧基中选择最多5个取代基，噻吩基选项地取代，每个取代基可独立地从卤素和C1-C4烷基中选择最多3个取代基，以及C2-C8烷基、C2-C8烯基、C3-C8环烷基和C4-C8环烷基烷基，每个基可选地取代，每个取代基可独立地从卤素、C1-C4烷基、C1-C4烷氧基、C1-C4烷基-S(O)n-（其中n为0、1或2）、-CF3、-CN和-CONH2中选择；Y从苯基、萘基、二氢苯并噻吩基、苯并噻唑基、苯并异噻唑基、喹啉基、异喹啉基、萘啉基、噻吩吡啉基、茚基、1,3-苯并二氧杂环戊基、苯并噻吩基、吲哚基和苯并呋喃基中选择，每个基可选地取代，最多可独立地从卤素、C1-C4烷基、C1-C4烷氧基、C1-C4烷基-S(O)n-（其中n为0、1或2）、硝基、乙酰基、-CF3、-SCF3和氰基中选择最多4个或在可能的情况下最多5个取代基；当Y为吲哚基时，它可以被取代或进一步被N-取代基取代，N-取代基从C1-C4烷基中选择；Z从OR3或F中选择，其中R3从H、C1-C6烷基和苯基C1-C6烷基中选择；R1和R2各自独立地为H或C1-C4烷基；以及其药学上可接受的盐，但有一个条件，即当Y为可选地取代的苯基或可选地取代的1,3-苯并二氧杂环戊基，Z为OR3且X为可选地取代的苯基时，A为-S-。
• [EN] 3-ARYLOXY/THIO-3-SUBSTITUTED PROPANAMINES AND THEIR USE IN INHIBITING SEROTONIN AND NOREPHINEPHRINE REUPTAKE<br/>[FR] COMPOSES PHARMACEUTIQUES
  申请人：LILLY CO ELI

  公开号：WO2004043904A1

  公开（公告）日：2004-05-27

  There is provided a compound of formula (I) wherein A is selected from -O- and -S-; X is selected from C2-C8 alkyl, C2-C8 alkenyl, C3-C8 cycloalkyl and C4-C8 cycloalkylalkyl, each of which may be optionally substituted with up to 3 substituents each independently selected from halo, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkyl-S(O)n- where n is 0, 1 or 2, -CF3, -CN and -CONH2; Y is selected from phenyl, naphthyl, dihydrobenzothienyl, benzothiazolyl, benzoisothiazolyl, quinolyl, isoquinolyl, naphthyridyl, thienopyridyl, indanyl, 1,3-benzodioxolyl, benzothienyl, indolyl and benzofuranyl, each of which may be optionally substituted with up to 4 or, where possible, 5 substituents each independently selected from halo, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkyl-S(O)n- where n is 0, 1 or 2, nitro, acetyl, -CF3, -SCF3 and cyano; and when Y is indolyl it may be substituted or further substituted by an N-substituent selected from C1-C4 alkyl; Z is selected from H, OR3 or F, wherein R3 is selected from H, C1-C6 alkyl and phenyl C1-C6 alkyl; R1 and R2 are each independently H or C1-C4 alkyl; with the proviso that, when Z is H, then Y may not be optionally substituted phenyl or optionally substituted naphthyl.

  提供一种具有以下结构的化合物（I）：其中A从-O-和-S-中选择；X从C2-C8烷基，C2-C8烯基，C3-C8环烷基和C4-C8环烷基烷基中选择，每种基团可能分别被选自卤素，C1-C4烷基，C1-C4烷氧基，C1-C4烷基-S(O)n-（其中n为0，1或2），-CF3，-CN和-CONH2的最多3个取代基所取代；Y从苯基，萘基，二氢苯并噻吩基，苯并噻唑基，苯并异噻唑基，喹啉基，异喹啉基，萘啉基，噻吩吡啉基，茚基，1,3-苯并二氧杂环戊基，苯并噻吩基，吲哚基和苯并呋喃基中选择，每种基团可能分别被选自卤素，C1-C4烷基，C1-C4烷氧基，C1-C4烷基-S(O)n-（其中n为0，1或2），硝基，乙酰基，-CF3，-SCF3和氰基的最多4个或在可能的情况下5个取代基所取代；当Y为吲哚基时，它可以被选自C1-C4烷基的N-取代基取代或进一步取代；Z从H，OR3或F中选择，其中R3从H，C1-C6烷基和苯基C1-C6烷基中选择；R1和R2分别独立地为H或C1-C4烷基；但是，当Z为H时，Y可能不是可选择地取代的苯基或可选择地取代的萘基。
• Compounds useful in the complement, coagulat and kallikrein pathways and method for their preparation
  申请人：BioCryst Pharmaceuticals, Inc.

  公开号：US06653340B1

  公开（公告）日：2003-11-25

  The present invention is concerned with new compounds, and particularly those having a fused bicyclic ring substituted with an amidine moiety. These compounds are each potent inhibitors of Factor D of the alternate pathway of complement, C1s of the classical pathway of complement, Factors Xa, XIIa, VIIa and thrombin of the coagulation pathway, plasmin in the fibrinolytic pathway, and kallikrein and high molecular weight kininogen in the inflammatory pathways. These proteases, which have serine in their active site, are called serine proteases and they are pivotal to most of the processes of inflammation and coagulation. In fact, these various systems are interactive with one another and it is difficult to activate one pathway without it influencing the others.

  本发明涉及新化合物，特别是那些具有被取代的酰胺基团的融合双环环的化合物。这些化合物分别是替代途径的因子D、经典途径的C1s、凝血途径的因子Xa、XIIa、VIIa和凝血酶、纤溶途径的纤溶酶、以及炎症途径的激肽酶和高分子量激肽原的强效抑制剂。这些蛋白酶，在其活性位点中含有丝氨酸，被称为丝氨酸蛋白酶，它们对大多数炎症和凝血过程至关重要。事实上，这些各种系统彼此之间相互作用，很难激活其中一个途径而不影响其他途径。
• [EN] HETEROARYLOXY 3-SUBSTITUTED PROPANAMINES S SEROTONIN AND NOREPINEPHRINE REUPTAKE INHIBITORS<br/>[FR] PROPANAMINES SUBSTITUEES EN 3 PAR UN HETEROARYLOXY UTILISEES EN TANT QU'INHIBITEURS DE RECAPTAGE DE SEROTONINE ET DE NOREPINEPHRINE
  申请人：LILLY CO ELI

  公开号：WO2002094262A1

  公开（公告）日：2002-11-28

  There is provided a heretoaryloxy 3-substituted propanamine compound of formula (I): wherein A is selected from -O- and -S-; X is selected from phenyl optionally substituted with up to 5 substituents selected from halo, C1-C4 alkyl and C1-C4 alkoxy, and thienyl optionally substituted with up to 3 substituents selected from halo and C1-C4 alkyl; Y is selected from benzothienyl, indolyl and benzofuranyl, optionally substituted with up to 5 substituents selected from halo, C1-C4 alkyl, C1-C4 alkoxy, nitro, acetyl and cyano; and when Y is indolyl it may be substituted or further substituted by an N-substituent selected from C1-C4 alkyl; R1 and R2 are each independently H or C1-C4 alkyl; and pharmaceutically acceptable salts thereof.

  提供了一种公式（I）的取代了3-丙胺基的芳氧基化化合物，其中A选自-O-和-S-; X选自苯基，可选地取代高达5个卤素、C1-C4烷基和C1-C4烷氧基，以及噻吩基，可选地取代高达3个卤素和C1-C4烷基; Y选自苯并噻吩基、吲哚基和苯并呋喃基，可选地取代高达5个卤素、C1-C4烷基、C1-C4烷氧基、硝基、乙酰基和氰基; 当Y为吲哚基时，它可以被C1-C4烷基的N取代或进一步取代; R1和R2各自独立地为H或C1-C4烷基;以及其药学上可接受的盐。
• 3-Aryloxy/thio-3-substituted propanamines and their use in inhibiting serotonin and norephinephrine reuptake
  申请人：Boulet Louis Serge

  公开号：US20060014779A1

  公开（公告）日：2006-01-19

  There is provided a compound of formula (I) wherein A is selected from —O— and —S—; X is selected from C 2 -C 8 alkyl, C 2 -C 8 alkenyl, C 3 -C 8 cycloalkyl and C 4 -C 8 cycloalkylalkyl, each of which may be optionally substituted with up to 3 substituents each independently selected from halo, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkyl-S(O) n — where n is 0, 1 or 2 , —CF 3 , —CN and —CONH 2 ; Y is selected from phenyl, naphthyl, dihydrobenzothienyl, benzothiazolyl, benzoisothiazolyl, quinolyl, isoquinolyl, naphthyridyl, thienopyridyl, indanyl, 1,3 -benzodioxolyl, benzothienyl, indolyl and benzofuranyl, each of which may be optionally substituted with up to 4 or, where possible, 5 substituents each independently selected from halo, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkyl-S(O) n — where n is 0, 1 or 2 , nitro, acetyl, —CF 3 , —SCF 3 and cyano; and when Y is indolyl it may be substituted or further substituted by an N-substituent selected from C 1 -C 4 alkyl; Z is selected from H, OR 3 or F, wherein R 3 is selected from H, C 1 -C 6 alkyl and phenyl C 1 -C 6 alkyl; R 1 and R 2 are each independently H or C 1 -C 4 alkyl; with the proviso that, when Z is H, then Y may not be optionally substituted phenyl or optionally substituted naphthyl.

  提供了一种化合物，其化学式为（I），其中A从—O—和—S—中选择；X从C2-C8烷基，C2-C8烯基，C3-C8环烷基和C4-C8环烷基烷基中选择，每种基团均可选用最多3个取代基，每个取代基可独立地从氯，C1-C4烷基，C1-C4烷氧基，C1-C4烷基-S（O）n-其中n为0，1或2，—CF3，—CN和—CONH2中选择；Y从苯基，萘基，二氢苯并噻吩基，苯并噻唑基，苯并异噻唑基，喹啉基，异喹啉基，萘啉基，噻吩基，茚基，1,3-苯并二氧杂环基，苯并噻吩基，吲哚基和苯并呋喃基中选择，每种基团均可选用最多4个或在可能的情况下最多5个取代基，每个取代基可独立地从氯，C1-C4烷基，C1-C4烷氧基，C1-C4烷基-S（O）n-其中n为0，1或2，硝基，乙酰基，—CF3，—SCF3和氰基中选择；当Y为吲哚基时，它可以被一个N-取代基所取代，所述取代基从C1-C4烷基中选择；Z从H，OR3或F中选择，其中R3从H，C1-C6烷基和苯基C1-C6烷基中选择；R1和R2各自独立地为H或C1-C4烷基；但是，当Z为H时，Y可能不是可选取代的苯基或可选取代的萘基。