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7-fluoro-5-(methylsulfonyl)-2,3-dihydro-1H-indole hydrochloride | 1240301-82-9

中文名称
——
中文别名
——
英文名称
7-fluoro-5-(methylsulfonyl)-2,3-dihydro-1H-indole hydrochloride
英文别名
7-fluoro-5-methylsulfonyl-2,3-dihydro-1H-indole;hydrochloride
7-fluoro-5-(methylsulfonyl)-2,3-dihydro-1H-indole hydrochloride化学式
CAS
1240301-82-9
化学式
C9H10FNO2S*ClH
mdl
——
分子量
251.709
InChiKey
XPITXZKBJSQDSZ-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    1.62
  • 重原子数:
    15
  • 可旋转键数:
    1
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.33
  • 拓扑面积:
    54.6
  • 氢给体数:
    2
  • 氢受体数:
    4

反应信息

  • 作为反应物:
    描述:
    7-fluoro-5-(methylsulfonyl)-2,3-dihydro-1H-indole hydrochloride吡啶三氟乙酸 作用下, 以 乙醚 为溶剂, 反应 19.0h, 生成 2-(piperidin-4-yl)propyl 7-fluoro-5-(methylsulfonyl)-2,3-dihydro-1H-indole-1-carboxylate
    参考文献:
    名称:
    Discovery of a novel series of indoline carbamate and indolinylpyrimidine derivatives as potent GPR119 agonists
    摘要:
    GPR119 has emerged as an attractive target for anti-diabetic agents. We identified a structurally novel GPR119 agonist 22c that carries a 5-(methylsulfonyl) indoline motif as an early lead compound. To generate more potent compounds of this series, structural modifications were performed mainly to the central alkylene spacer. Installation of a carbonyl group and a methyl group on this spacer significantly enhanced agonistic activity, resulting in the identification of 2-[1-(5-ethylpyrimidin-2-yl)piperidin-4-yl] propyl 7-fluoro-5-(methylsulfonyl)-2,3-dihydro-1H-indole-1-carboxylate (20). To further expand the chemical series of indoline-based GPR119 agonists, several heterocyclic core systems were introduced as surrogates of the carbamate spacer that mimic the presumed active conformation. This approach successfully produced an indolinylpyrimidine derivative 37, 5-(methylsulfonyl)-1-[6-({1-[3-(propan-2-yl)-1,2,4-oxadiazol-5-yl]piperidin-4-yl}oxy)pyrimidin-4-yl]-2,3-dihydro-1H-indole, which has potent GPR119 agonist activity. In rat oral glucose tolerance tests, these two indoline-based compounds effectively lowered plasma glucose excursion and glucose-dependent insulin secretion after oral administration. (C) 2014 Elsevier Ltd. All rights reserved.
    DOI:
    10.1016/j.bmc.2014.01.028
  • 作为产物:
    描述:
    参考文献:
    名称:
    Discovery of a novel series of indoline carbamate and indolinylpyrimidine derivatives as potent GPR119 agonists
    摘要:
    GPR119 has emerged as an attractive target for anti-diabetic agents. We identified a structurally novel GPR119 agonist 22c that carries a 5-(methylsulfonyl) indoline motif as an early lead compound. To generate more potent compounds of this series, structural modifications were performed mainly to the central alkylene spacer. Installation of a carbonyl group and a methyl group on this spacer significantly enhanced agonistic activity, resulting in the identification of 2-[1-(5-ethylpyrimidin-2-yl)piperidin-4-yl] propyl 7-fluoro-5-(methylsulfonyl)-2,3-dihydro-1H-indole-1-carboxylate (20). To further expand the chemical series of indoline-based GPR119 agonists, several heterocyclic core systems were introduced as surrogates of the carbamate spacer that mimic the presumed active conformation. This approach successfully produced an indolinylpyrimidine derivative 37, 5-(methylsulfonyl)-1-[6-({1-[3-(propan-2-yl)-1,2,4-oxadiazol-5-yl]piperidin-4-yl}oxy)pyrimidin-4-yl]-2,3-dihydro-1H-indole, which has potent GPR119 agonist activity. In rat oral glucose tolerance tests, these two indoline-based compounds effectively lowered plasma glucose excursion and glucose-dependent insulin secretion after oral administration. (C) 2014 Elsevier Ltd. All rights reserved.
    DOI:
    10.1016/j.bmc.2014.01.028
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文献信息

  • FUSED HETEROCYCLIC RING COMPOUND
    申请人:Takeda Pharmaceutical Company Limited
    公开号:EP2399914A1
    公开(公告)日:2011-12-28
    A compound represented by the following formula or a salt thereof, which has an GPR119 agonist action, is useful for the prophylaxis or treatment of diabetes, obesity and the like, and shows superior efficacy: wherein P: substituted 6-membered aromatic ring, Q: (substituted) 6-membered aromatic ring, A1: CR4aR4b, NR4c, O, S, SO or SO2 R4a-4c: H etc.}, L1: (substituted) C1-5 alkylene, L2: a bond or (substituted) C1-3 alkylene, L3-4: (substituted) C1-3 alkylene, R1: H, X, CN, (substituted) hydrocarbon, (substituted) heterocycle or (substituted) OH, or (substituted) 4- to 8-membered (heterocyclic) ring together with A1, R2: H, CN, (substituted) hydrocarbon, and R3a: -COSRA1, (substituted) 5- or 6-membered aromatic ring RA1: (substituted) hydrocarbon or (substituted) heterocycle}.
    下式所代表的化合物或其盐具有 GPR119 激动剂的作用,可用于预防或治疗糖尿病、肥胖症等,并显示出卓越的疗效: 其中 P:取代的 6 元芳香环、 Q:(取代的)6 元芳香环、 A1:CR4aR4b、NR4c、O、S、SO 或 SO2 R4a-4c:H等}、 L1:(取代的)C1-5 亚烷基、 L2:键或(取代的)C1-3 亚烷基、 L3-4:(取代的)C1-3 亚烷基、 R1:H、X、CN、(取代的)烃、(取代的)杂环或(取代的)OH,或与 A1 一起的(取代的)4-8 元(杂环)环、 R2:H、CN、(取代的)烃,以及 R3a:-COSRA1、(取代的)5 或 6 元芳香环 RA1:(取代的)烃或(取代的)杂环}。
  • EP2399914
    申请人:——
    公开号:——
    公开(公告)日:——
  • US8410089B2
    申请人:——
    公开号:US8410089B2
    公开(公告)日:2013-04-02
  • Discovery of a novel series of indoline carbamate and indolinylpyrimidine derivatives as potent GPR119 agonists
    作者:Kenjiro Sato、Hiromichi Sugimoto、Kentaro Rikimaru、Hiroshi Imoto、Masahiro Kamaura、Nobuyuki Negoro、Yoshiyuki Tsujihata、Hirohisa Miyashita、Tomoyuki Odani、Toshiki Murata
    DOI:10.1016/j.bmc.2014.01.028
    日期:2014.3
    GPR119 has emerged as an attractive target for anti-diabetic agents. We identified a structurally novel GPR119 agonist 22c that carries a 5-(methylsulfonyl) indoline motif as an early lead compound. To generate more potent compounds of this series, structural modifications were performed mainly to the central alkylene spacer. Installation of a carbonyl group and a methyl group on this spacer significantly enhanced agonistic activity, resulting in the identification of 2-[1-(5-ethylpyrimidin-2-yl)piperidin-4-yl] propyl 7-fluoro-5-(methylsulfonyl)-2,3-dihydro-1H-indole-1-carboxylate (20). To further expand the chemical series of indoline-based GPR119 agonists, several heterocyclic core systems were introduced as surrogates of the carbamate spacer that mimic the presumed active conformation. This approach successfully produced an indolinylpyrimidine derivative 37, 5-(methylsulfonyl)-1-[6-(1-[3-(propan-2-yl)-1,2,4-oxadiazol-5-yl]piperidin-4-yl}oxy)pyrimidin-4-yl]-2,3-dihydro-1H-indole, which has potent GPR119 agonist activity. In rat oral glucose tolerance tests, these two indoline-based compounds effectively lowered plasma glucose excursion and glucose-dependent insulin secretion after oral administration. (C) 2014 Elsevier Ltd. All rights reserved.
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