5-溴-1H-[1,6]二氮杂萘-2-酮 | 105276-96-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 5-溴-1H-[1,6]二氮杂萘-2-酮
• 英文名称: 5-bromo-1,6-naphthyridin-2(1H)-one
• 英文别名: 5-bromo-1H-1,6-naphthyridin-2-one
• CAS: 105276-96-8
• 化学式: C₈H₅BrN₂O
• 分子量: 225.044
• InChiKey: HBOWEWFBGYLXNY-UHFFFAOYSA-N

物化性质

• 沸点：
  435.5±45.0 °C(Predicted)
• 密度：
  1.711±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 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：
  42
• 氢给体数：
  1
• 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：

  5-溴-1H-[1,6]二氮杂萘-2-酮 生成 5-(4-nitro-1H-imidazol-1-yl)-1,6-naphthyridin-2(1H)-one
  参考文献：
  名称：

  LESHER, GEORGE Y.;SINGH, BALDEV

  摘要：

  DOI：
• 作为产物：
  描述：

  2-<2-(dimethylamino)ethenyl>-1,6-dihydro-6-oxo-3-pyridinecarbonitrile 在 氢溴酸 作用下， 以 氯仿 、 溶剂黄146 为溶剂， 以94%的产率得到5-溴-1H-[1,6]二氮杂萘-2-酮
  参考文献：
  名称：

  Novel cAMP PDE III inhibitors: 1,6-naphthyridin-2(1H)-ones

  摘要：

  Two series of medorinone (3) analogs were prepared by modifications at C(2) and C(5). The C(2)-series was prepared from 2-chloro-5-methyl-1,6-naphthyridine (4) by replacement of the chloro group with various nucleophiles. The C(5)-series was prepared from 5-acyl-6-[2-(dimethylamino)ethenyl]-2-(1H)-pyridinone (11), 5-bromo-1,6-naphthyridin-2(1H)-one (17), and 1,3-diketones 19 and 27. 1,6-Naphthyridin-2(1H)-ones are novel inhibitors of cAMP PDE III. Modification of the carbonyl group of 3 or N-methylation at N(1) resulted in a dramatic loss of enzyme activity. Absence of the C(5)-methyl group of medorinone (3) or its shift to C(3) or C(7) also resulted in reduced activity. Substitution at C(3) also diminished activity. However, substitution at C(5) by a wide variety of substituents led to improvement of enzyme activity and several C(5)-substituted analogs were more potent than milrinone.

  DOI：

  10.1021/jm00104a012

文献信息

• 2-[2-(di-lower-alkylamino)-1
  申请人：Sterling Drug Inc.

  公开号：US04634772A1

  公开（公告）日：1987-01-06

  2-[2-(di-lower-alkylamino-1-propenyl]-6-methoxy-3-pyridinecarbonitriles, useful as intermediates for cardiotonic agents.

  2-[2-(二烷基氨基-1-丙烯基)-6-甲氧基-3-吡啶碳腈，可用作心力衰竭药物的中间体。
• 1,6-naphthyridine-2(1H)-ones and their use as cardiotonic agents
  申请人：Sterling Drug Inc.

  公开号：US04657915A1

  公开（公告）日：1987-04-14

  5-X-7-R'-1,6-Naphthyridine-2(1H)-ones (formula II) or salts thereof, where X is bromo, chloro or hydrazino and R' is hydrogen or methyl, which are useful as cardiotonic agents.

  5-X-7-R'-1,6-萘啉并咪唑-2(1H)-酮（式II）或其盐，其中X为溴、氯或联氨基，R'为氢或甲基，可用作心力衰竭药物。
• 1,6-dihydro-6-oxo-3-pyridinecarbonitriles, intermediates for cardiotonic
  申请人：Sterling Drug Inc.

  公开号：US04697021A1

  公开（公告）日：1987-09-29

  5-[1H-(5-membered-N-aromatic-heteryl)-1-yl]-7-R'-1,6-naphthyridin-2(1H)-one s (formula I) or salts thereof are useful as cardiotonic agents. Also shown as intermediates are 5-X-7-R'-1,6-naphthyridin-2(1H)-ones (formula II) or salts thereof, where X is bromo, chloro or hydrazino, 2-[2-(di-lower-alkylamino)ethenyl]-1,6-dihydro-6-oxo-3-pyridinecarbonitril e (formula III), and 2-[2-(di-lower-alkylamino)-1-propenyl]-6-methoxy-3-pyridinecarbonitrile (formula IIIa). Processes shown include the preparation of I from II, preparation of II from III or IIIa and the preparation of III from 1,6-dihydro-2-methyl-6-oxo-3-pyridinecarbonitrile, and the preparation of IIIa from 6-methoxy-2-methyl-3-pyridinecarbonitrile.

  5-[1H-(5-成员-N-芳基杂环)-1-基]-7-R'-1,6-萘啶-2（1H）-酮（式I）或其盐可用作强心剂。还显示了5-X-7-R'-1,6-萘啶-2（1H）-酮（式II）或其盐的中间体，其中X为溴，氯或肼基，2-[2-（二-低烷基）氨基乙烯基]-1,6-二氢-6-氧基-3-吡啶羧腈（式III），以及2-[2-（二-低烷基）氨基-1-丙烯基]-6-甲氧基-3-吡啶羧腈（式IIIa）。所示的过程包括从II制备I，从III或IIIa制备II，从1,6-二氢-2-甲基-6-氧基-3-吡啶羧腈制备III，以及从6-甲氧基-2-甲基-3-吡啶羧腈制备IIIa。
• 5-[1H-(5-membered-N-aromatic heteryl)-1-yl]-1,6-naphthyridin-2(1H)-ones
  申请人：Sterling Drug Inc.

  公开号：US04716170A1

  公开（公告）日：1987-12-29

  5-[1H-(5-membered-N-aromatic-heteryl)-1-yl]-7-R'-1,6-naphthyridin-2(1H)-one s (formula I) or salts thereof are useful as cardiotonic agents. Also shown as intermediates are 5-X-7-R'-1,6-naphthyridin-2(1H)-ones (formula II) or salts thereof, where X is bromo, chloro or hydrazino, 2-[2-(di-lower-alkylamino)ethenyl]-1,6-dihydro-6-oxo-3-pyridinecarbonitril e (formula III), and 2-[2-(di-lower-alkylamino)-2-propenyl]-6-methoxy-3-pyridinecarbonitrile (formula IIIa). Processes shown include the preparation of I from II, preparation of II from III or IIIa and the preparation of III from 1,6-dihydro-2-methyl-6-oxo-3-pyridinecarbonitrile, and the preparation of IIIa from 6-methoxy-2-methyl-3-pyridinecarbonitrile.

  5-[1H-(5-成员-N-芳基杂环)-1-基]-7-R'-1,6-萘啶-2(1H)-酮（式I）或其盐可用作心力强效剂。5-X-7-R'-1,6-萘啶-2（1H）-酮（式II）或其盐，其中X为溴，氯或肼，2-[2-(二-低烷基)氨基乙烯基]-1,6-二氢-6-氧基-3-吡啶羧腈（式III）和2-[2-(二-低烷基)氨基丙烯基]-6-甲氧基-3-吡啶羧腈（式IIIa）也被用作中间体。所示的过程包括从II制备I，从III或IIIa制备II，从1,6-二氢-2-甲基-6-氧基-3-吡啶羧腈制备III以及从6-甲氧基-2-甲基-3-吡啶羧腈制备IIIa。
• 1,6-Naphthyridin-2(1H)-ones having cardiotonic activity and preparation
  申请人：STERLING DRUG INC.

  公开号：EP0189853A2

  公开（公告）日：1986-08-06

  5-[1H-(5-membered-N-aromatic-heteryl)-1-yl]-7-R'-1,6-naphthyridin-2(1H)-ones (formula 1) or salts thereof are useful as cardiotonic agents. Also shown as intermediates are 5-X-7-R'-1,6-naphthyridin-2(1H)-ones (formula II) or salts thereof, where X is bromo, chloro or hydrazino, 2-[2-(di-lower-alkylamino)ethenyl)-1,6-dihydro-6-oxo-3-pyridinecarbonitrile (formula III), and 2-[2-(di-lower- alkylamino)-1-propenyl]-6-methoxy-3-pyridinecarbonitrile (formula IIIa). Processes shown include the preparation of I from II, preparation of II from III or IIIa and the preparation of III from 1,6-dihydro-2-methyl-6-oxo-3-pyridinecarbonitrile, and the preparation of IIIa from 6-methoxy-2-methyl-3-pyridinecarbonitrile.

  5-[1H-(5-membered-N-aromatic-heteryl)-1-yl]-7-R'-1,6-萘啶-2(1H)-酮（式 1）或其盐可用作强心剂。作为中间体的还有 5-X-7-R'-1,6-萘啶-2(1H)-酮（式 II）或其盐（其中 X 为溴代、氯代或肼代）、2-[2-（二低级烷基氨基）乙烯基]-1,6-二氢-6-氧代-3-吡啶甲腈（式 III）和 2-[2-（二低级烷基氨基）-1-丙烯基]-6-甲氧基-3-吡啶甲腈（式 IIIa）。所示工艺包括由 II 制备 I，由 III 或 IIIa 制备 II，由 1,6-二氢-2-甲基-6-氧代-3-吡啶甲腈制备 III，以及由 6-甲氧基-2-甲基-3-吡啶甲腈制备 IIIa。