2,2-bis(fluoromethyl)-3,4-dihydro-6-nitro-2H-1-benzopyran-4-one | 147402-37-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2,2-bis(fluoromethyl)-3,4-dihydro-6-nitro-2H-1-benzopyran-4-one
• 英文别名: 2,2-bisfluoromethyl-3,4-dihydro-6-nitro-2H-1-benzopyran-4-one；2,2-bis(fluoromethyl)-6-nitro-3H-chromen-4-one
• CAS: 147402-37-7
• 化学式: C₁₁H₉F₂NO₄
• 分子量: 257.194
• InChiKey: AMWXTMAABNWDRG-UHFFFAOYSA-N

物化性质

• 沸点：
  414.5±45.0 °C(Predicted)
• 密度：
  1.374±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,2-bis(fluoromethyl)-3,4-dihydro-6-nitro-2H-1-benzopyran-4-one 在 吡啶 、 potassium iodide 、 stannous chloride 、 sodium chloride 、 硫酸 、 zinc diiodide 、 溶剂黄146 、 sodium nitrite 、 三氯氧磷 作用下， 以 二氯甲烷 、 水 、 苯 为溶剂， 生成 2,2-bis(fluoromethyl)-6-iodo-2H-1-benzopyran-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  Remedies for peripheral circulation disturbances

  摘要：

  本发明的目的是为外周血管疾病提供新型治疗药物。 本发明提供了包含一种通式（1）的苯并吡喃或苯并噁嗪衍生物的药物组合物： 其中； R1代表氢原子、较低的烷基或芳基，或R1直接与Q或R11结合形成单键； R2代表取代或未取代的氨基、饱和或不饱和的杂环基、A—O—或—C(═X)Y； Q代表═N—、N+—O−或C(R11)R12； R3和R4各自代表氢原子、较低的烷基或具有卤原子或较低的烷氧基等取代基的取代的较低烷基，R5和R6各自代表氢原子、卤原子、较低的烷基、较低的卤代烷基或类似物；以及一种药学上可接受的载体。

  公开号：

  US06248777B1
• 作为产物：
  描述：

  2-羟基-5-硝基苯乙酮 、 1,3-二氟丙酮 在 四氢吡咯 作用下， 以 苯 为溶剂， 反应 1.0h， 以56%的产率得到2,2-bis(fluoromethyl)-3,4-dihydro-6-nitro-2H-1-benzopyran-4-one
  参考文献：
  名称：

  6-Substituted 2,2-Bis(fluoromethyl)-benzopyran-4-carboxamide K + channel openers

  摘要：

  In the course of our study to find an ideal antihypertensive potassium channel opener (KCO), N-(2-cyanoethyl)-2,2 bis(fluoromethyl)-6-pentafluoroethyl-2H-1-benzopyran-4-carboxamide (13f, KC-515) showed a highly potent, slow and long-lasting antihypertensive effect with reduced reflex tachycardia, together with the beneficial effects of KCO such as improvement in lipid metabolism. These profiles identify KC-515 as a potential candidate. In conscious spontaneously hypertensive rats (SHR), the onset of the hypotensive effect of KC-515 (13f) was gradual and the maximum response was attained at around 6 h after dosing. The duration of action was over 18 h for 0.1 mg/kg. When administered to Zucker rats for 2 weeks with 0.03-0.3 mg/kg po range in the antihypertensive doses in hypertensive rat models, KC-515 (13f) significantly and dose-dependently reduced serum triglycerides to less than 70% of control without affecting total cholesterol. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00064-x

文献信息

• Benzopyran derivatives
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：US05874446A1

  公开（公告）日：1999-02-23

  Novel benzopyran and benzoxazine derivatives represented by the general formula: ##STR1## wherein R.sub.1 and R.sub.2 represent a lower haloalkyl group, R.sub.3 represents a hydrogen atom, etc., R.sub.4 represents a heterocyclic group or A--O-- wherein A represents a cyclic structure, etc., R.sub.5 and R.sub.6 represent a lower haloalkyl, X represents .dbd.N--, N.fwdarw.O, etc, are disclosed. These compounds exhibit K.sup.+ channel opening activating and can be widely used as an anti-asthma drug, an anti-epilepsy drug, etc.

  新型苯并吡喃和苯并噁嗪衍生物的一般公式表示为：##STR1##其中R.sub.1和R.sub.2代表较低的卤代烷基，R.sub.3代表氢原子，等等，R.sub.4代表杂环基或A--O--，其中A代表环状结构，等等，R.sub.5和R.sub.6代表较低的卤代烷基，X代表.dbd.N--，N.fwdarw.O等。这些化合物表现出K.sup.+通道开放激活作用，可广泛用作抗哮喘药物、抗癫痫药物等。
• Remedies for peripheral circulation disturbances
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：US06248777B1

  公开（公告）日：2001-06-19

  It is an object of the present invention to provide novel therapeutic agents for peripheral vascular disease. The present invention provides pharmaceutical compositions comprising a benzopyran or benzoxazine derivative of the general formula (1): wherein; R1 represents a hydrogen atom, a lower alkyl group or an aryl group, or R1 directly couples with Q or R11 to form a single bond; R2represents a substituted or unsubstituted amino group, a saturated or unsaturated heterocyclic group, A—O—or —C(═X)Y; Q represents ═N—, N+—O−or C(R11)R12; R3 and R4 each represent a hydrogen atom, a lower alkyl group or a substituted lower alkyl group having a halogen atom or a lower alkoxy group as a substituent or the like; and R5 and R6 each represent a hydrogen atom, a halogen atom, a lower alkyl group, a lower haloalkyl group or the like; and a pharmaceutically acceptable carrier.

  本发明的目的是为外周血管疾病提供新型治疗药物。 本发明提供了包含一种通式（1）的苯并吡喃或苯并噁嗪衍生物的药物组合物： 其中； R1代表氢原子、较低的烷基或芳基，或R1直接与Q或R11结合形成单键； R2代表取代或未取代的氨基、饱和或不饱和的杂环基、A—O—或—C(═X)Y； Q代表═N—、N+—O−或C(R11)R12； R3和R4各自代表氢原子、较低的烷基或具有卤原子或较低的烷氧基等取代基的取代的较低烷基，R5和R6各自代表氢原子、卤原子、较低的烷基、较低的卤代烷基或类似物；以及一种药学上可接受的载体。
• N-(2-cyanoethyl)-6-fluoroalkyl-2h-1-benzopyran derivatives
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：US05646310A1

  公开（公告）日：1997-07-08

  Described herein are benzopyran derivatives represented by the formula: ##STR1## wherein R, X and Y represent any of the following combinations: ______________________________________ R X Y ______________________________________ C.sub.2 F.sub.5 O H C.sub.2 F.sub.5 S H CF.sub.3 S F C.sub.2 F.sub.5 S F C.sub.3 F.sub.7 S F ______________________________________ PAL and pharmaceutically acceptable salts thereof. These compounds have an excellent potassium channel activity and are also excellent from the aspect of safety.

  本文描述了由以下公式表示的苯并吡喃衍生物：##STR1## 其中R、X和Y代表以下任意组合之一： ______________________________________ R X Y ______________________________________ C.sub.2 F.sub.5 O H C.sub.2 F.sub.5 S H CF.sub.3 S F C.sub.2 F.sub.5 S F C.sub.3 F.sub.7 S F ______________________________________ PAL及其药学上可接受的盐。这些化合物具有优异的钾通道活性，并且从安全性方面也表现出色。
• NOVEL BENZOPYRAN DERIVATIVE
  申请人：CHUGAI SEIYAKU KABUSHIKI KAISHA

  公开号：EP0632033A1

  公开（公告）日：1995-01-04

  A benzopyran derivative represented by general formula (I), which has a K⁺ channel activating function and thus can be widely applied as antiasthmatic, antiepileptic, and so forth. In formula (I), R₁ represents hydrogen or hydroxy; R₂ and R₃ represent each lower alkyl, etc.; R₄ and R₅ represent each hydrogen, lower haloalkyl, halogeno, nitro, etc.; X represents =O, =S, = N-CN, etc.; and Y represents hydroxy, substituted amino, etc.

  一种由通式(I)代表的苯并吡喃衍生物，它具有激活 K⁺通道的功能，因此可广泛应用于抗哮喘、抗癫痫等方面。在式（I）中，R₁ 代表氢或羟基；R₂ 和 R₃ 分别代表低级烷基等；R₄ 和 R₅ 分别代表氢、低级卤代烷基、卤代、硝基等；X 代表＝O、＝S、＝N-CN 等；Y 代表羟基、取代氨基等。
• BENZOPYRAN AND BENZOXAZINE DERIVATIVES
  申请人：CHUGAI SEIYAKU KABUSHIKI KAISHA

  公开号：EP0655448A1

  公开（公告）日：1995-05-31

  Benzopyran and benzoxazine derivatives represented by general formula (I) and the use thereof as a K⁺ channel activator for treating asthma, epilepsy and so forth, wherein R₁ and R₂ represent each lower haloalkyl; R₃ represents hydrogen, etc.; R₄ represents a heterocyclic group, A-O- (A being a ring structure), etc.; R₅ and R₆ represent each lower haloalkyl; and X represents =N-, N->O or (II) (R₇ and R₈ being each hydrogen, hydroxyl, etc.).

  通式(I)代表的苯并吡喃和苯并噁嗪衍生物及其作为治疗哮喘、癫痫等的 K⁺ 通道激活剂的用途，其中 R₁ 和 R₂ 各自代表低级卤代烷基；R₃ 代表氢等。R₄ 代表杂环基、A-O-（A 为环状结构）等；R₅ 和 R₆ 分别代表低级卤代烷基；X 代表 =N-、N->O 或 (II) （R₇ 和 R₈ 分别为氢、羟基等）。