6-benzoyl-2,2-dimethyl-2H-1-benzopyran | 91735-45-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-benzoyl-2,2-dimethyl-2H-1-benzopyran
• 英文别名: (2,2-Dimethylchromen-6-yl)-phenyl-methanone；(2,2-dimethylchromen-6-yl)-phenylmethanone
• CAS: 91735-45-4
• 化学式: C₁₈H₁₆O₂
• 分子量: 264.324
• InChiKey: SRJSZUCPXFCGAL-UHFFFAOYSA-N

物化性质

• 沸点：
  413.3±45.0 °C(Predicted)
• 密度：
  1.114±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-benzoyl-2,2-dimethyl-2H-1-benzopyran 在 ammonium hydroxide 、 sodium hypochlorite 、 4-苯基吡啶-N-氧化物 、 Jacobsen's catalyst 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 60.0h， 生成 2-[(3S,4R)-6-benzoyl-3-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl]-1-(4-chlorophenyl)-3-cyanoguanidine
  参考文献：
  名称：

  Cardioselective Antiischemic ATP-Sensitive Potassium Channel (K_ATP) Openers. 6. Effect of Modifications at C6 of Benzopyranyl Cyanoguanidines

  摘要：

  The effect on potency and selectivity of modifications at the C6 position of the cardioprotective K-ATP Opener BMS-180448 (2) is described. Structure-activity studies show that a variety of electron-withdrawing groups (ketone, sulfone, sulfonamide, etc.) are tolerated for cardioprotective activity as measured by EC25 values for an increase in time to the onset of contracture in globally ischemic rat, hearts. Changes made to the sulfonamido substituent indicate that compounds derived from secondary lipophilic amines are preferred for good cardioprotective potency and selectivity. The diisobutyl analogue 27 (EC25 = 0.04 mu M) is the most potent compound of this series. The cardiac selectivity of 27 results from a combination of reduced vasorelaxant potency and enhanced cardioprotective potency relative to the potent vasodilating K-ATP openers (e.g., cromakalim). The diisobutylsulfonamide analogue 27 is over 4 orders of magnitude more cardiac selective than cromakalim (1), These results support the hypothesis that the cardioprotective and vasorelaxant properties of K-ATP openers follow distinct structure-activity relationships. The mechanism of action of 27 appears to involve opening of the cardiac K-ATP as its cardioprotective effects are abolished by the K-ATP blocker glyburide.

  DOI：

  10.1021/jm990196h
• 作为产物：
  描述：

  4-羟基-二苯甲酮 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 copper dichloride 作用下， 以 邻二氯苯 、 乙腈 为溶剂， 反应 17.0h， 生成 6-benzoyl-2,2-dimethyl-2H-1-benzopyran
  参考文献：
  名称：

  Synthesis and antimycobacterial evaluation of benzofurobenzopyran analogues

  摘要：

  We recently reported that 3,3-dimethyl-3H-benzofuro[3,2,f][1]-benzopyran and its hydrogenated analogue are selective in vitro inhibitors of mycobacterial growth. However, their lack of in vivo activity on a murine model of Mycobacterium tuberculosis infection due to their poor bioavailability led to a structure-activity relationship investigation. We wish to report here the preparation of some structural analogues along with their biological effect on the growth of Mycobacterium smegmatis, M. tuberculosis, as well as on VERO cells for the most active compound. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.12.009

文献信息

• NOVEL BENZOPYRAN DERIVATIVES AS POTASSIUM CHANNEL OPENERS
  申请人：Zhang Xuqing

  公开号：US20070049556A1

  公开（公告）日：2007-03-01

  The present invention is directed to novel benzopyran derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders related to potassium channel.

  本发明涉及新型苯并吡喃衍生物，含有它们的药物组合物以及它们在治疗与钾通道相关的疾病中的应用。
• 6-Benzoyl-substituierte 3,4-Dihydro-2H-benzopyrane, Verfahren zu ihrer Herstellung, ihre Verwendung sowie pharmazeutische Präparate auf Basis dieser Verbindungen
  申请人：HOECHST AKTIENGESELLSCHAFT

  公开号：EP0355565A1

  公开（公告）日：1990-02-28

  Verbindung I mit R¹ gleich H, Alkoxy, Alkyl, NR⁴R⁵ und R²,R³ gleich H, Alkyl oder gemeinsam eine Kette, Ar ein gegebenenfalls substituierter Aromat, X eine (CH₂)-Kette haben hervorragende Wirksamkeit als Antihypertensiva, als Coronartherapeutika, als Mittel zur Behandlung der Herzinsuffizienz, der cerebralen bzw. peripheren Durchblutungsstörungen oder von Darmmotilitätsstörungen, vorzeitiger Wehentätigkeit, Obstruktionen der Atemwege oder der ableitenden harnwege oder der Gallenwege oder als Spasmolytika.

  化合物 I 中的 R¹ 为 H、烷氧基、烷基、NR⁴R⁵，R²,R³ 为 H、烷基或同为一条链，Ar 为任选取代的芳香族，X 为 (CH₂) 链，作为抗高血压药、冠心病治疗药、治疗心功能不全、脑或外周循环障碍或肠道运动障碍、早产、呼吸道或泌尿道梗阻或胆道梗阻的药物或解痉药，具有极佳的疗效。 如外周循环障碍或肠道运动障碍、早产、呼吸道或泌尿道或胆道阻塞，或作为解痉剂。
• Discovery and structure–activity relationships of a novel series of benzopyran-based KATP openers for urge urinary incontinence
  作者：Xuqing Zhang、Yuhong Qiu、Xiaojie Li、Sheela Bhattacharjee、Morgan Woods、Patricia Kraft、Scott G. Lundeen、Zhihua Sui

  DOI：10.1016/j.bmc.2008.11.055

  日期：2009.1

  A novel series of benzopyran derivatives were synthesized and evaluated as K(ATP) channel openers. Structure-activity relationships were investigated around 4-position of the benzopyran nucleus. Optimization of 4-substituent with some heterocyclic rings led to compound 13b bearing a benzo[d] isoxazol-3-one moiety as a potent and selective KATP channel opener in vitro. In two anesthetized rat models of myogenic bladder overactivity, compound 13b was found to inhibit spontaneous bladder contractions. (C) 2008 Elsevier Ltd. All rights reserved.
• Ahluwalia, V. K.; Singh, Raj P.; Singh, Rishi P., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1984, vol. 23, # 1, p. 42 - 45
  作者：Ahluwalia, V. K.、Singh, Raj P.、Singh, Rishi P.

  DOI：——

  日期：——
• Selenium-Based Solid-Phase Synthesis of Benzopyrans II: Applications to Combinatorial Synthesis of Medicinally Relevant Small Organic Molecules
  作者：K. C. Nicolaou、Guo-Qiang Cao、Jeffrey A. Pfefferkorn

  DOI：10.1002/(sici)1521-3773(20000218)39:4<739::aid-anie739>3.0.co;2-z

  日期：2000.2.18