2,2-dimethyl-2H-1-benzopyran-6-sulfonyl chloride | 185316-64-7

• 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-dimethyl-2H-1-benzopyran-6-sulfonyl chloride
• 英文别名: 2,2-Dimethylchromene-6-sulfonyl chloride
• CAS: 185316-64-7
• 化学式: C₁₁H₁₁ClO₃S
• 分子量: 258.726
• InChiKey: IRXSEERFLVHRBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-2H-1-benzopyran-6-sulfonyl chloride 在 ammonium hydroxide 、 sodium hypochlorite 、 4-苯基吡啶-N-氧化物 、 Jacobsen's catalyst 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 异丙醇 为溶剂， 反应 44.0h， 生成 (3S,4R)-4-Amino-3-hydroxy-2,2-dimethyl-chroman-6-sulfonic acid phenylamide
  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：

  6-溴-2,2-二甲基-2H-苯并吡喃 在 正丁基锂 、 磺酰氯 、 二氧化硫 作用下， 生成 2,2-dimethyl-2H-1-benzopyran-6-sulfonyl chloride
  参考文献：
  名称：

  A convenient Synthesis of 6-Substituted-2,2-Dimethyl-2H-1-Benzopyrans

  摘要：

  Various 2,2-dimethyl-6-functional-2H-1-benzopyrans were prepared via a halogen-metal exchange reaction followed by treatment with electrophiles. These 6-functionalized chromenes are important synthetic intermediates for preparation of benzopyran-based potassium channel openers.

  DOI：

  10.1080/00397919608004664

文献信息

• Sulfonamido substituted benzopyran derivatives
  申请人：Bristol-Myers Squibb Company

  公开号：US05869478A1

  公开（公告）日：1999-02-09

  ##STR1## and pharmaceutically acceptable salts thereof wherein Y is a single bond, --CH.sub.2 --, --C(O)--, --O--, --S-- or --N(R.sup.14)--; and R.sup.1 to R.sup.7 are as defined herein. These compounds have potassium channel activating activity and are useful, therefore for example, as cardiovascular agents.

  本发明涉及化合物及其药物学上可接受的盐，其中化合物的结构式如下：##STR1## 其中Y是单键，--CH.sub.2 --，--C（O）--，--O--，--S--或--N（R.sup.14）--；R.sup.1至R.sup.7如本文所定义。这些化合物具有钾通道激活活性，因此例如可用作心血管药物。
• Sulfonamido substituted benzopyran potassium channel activators
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：EP0747374A1

  公开（公告）日：1996-12-11

  The invention refers to compounds of the following formula and pharmaceutically acceptable salts thereof wherein Y is a single bond, -CH2- , -C(O)-, -O- , -S- or -N(R14)-. These compounds have potassium channel activating activity and are useful, therefore for example, as cardiovascular agents.

  本发明涉及下式化合物 及其药学上可接受的盐类，其中 Y 为单键、-CH2-、-C(O)-、-O-、-S- 或 -N(R14)-。 这些化合物具有激活钾通道的活性，因此可用作心血管药物等。
• Benzopyran sulfonamides as KV1.5 potassium channel blockers
  作者：John Lloyd、Karnail S. Atwal、Heather J. Finlay、Michael Nyman、Tram Huynh、Rao Bhandaru、Alexander Kover、Joan Schmidt、Wayne Vaccaro、Mary Lee Conder、Tonya Jenkins-West、Paul Levesque

  DOI：10.1016/j.bmcl.2007.04.020

  日期：2007.6

  K-v 1.5 blockers have the potential to be atrium-selective agents for treatment of atrial fibrillation. The benzopyrans provide a template for the synthesis of potent and selective K-v 1.5 blockers. (c) 2007 Elsevier Ltd. All rights reserved.
• US5869478A
  申请人：——

  公开号：US5869478A

  公开（公告）日：1999-02-09
• [EN] BENZOPYRANS HAVING POTASSIUM CHANNEL OPENING ACTIVITY<br/>[FR] BENZOPYRANNES POSSEDANT UNE ACTIVITE D'OUVERTURE DES CANAUX A POTASSIUM
  申请人：NOVARTIS AG

  公开号：WO2000021957A1

  公开（公告）日：2000-04-20

  A compound of formula (I) where the indicated OH group in the 3- position is in the trans position with respect to R?3, and R1 and R2¿ are independently hydrogen or C¿1? to C5 alkyl, R?3¿ is a group of the formula: -N(R6)-COR7 where R6 is hydrogen or C¿1? to C5 alkyl and R?7¿ is a C¿6? to C10 monovalent aromatic group or a monovalent heteroaromatic group having a 5- or 6-membered heteroaromatic ring, or R?6 and R7¿ together are 1,3-butadienylene or denote a group of formula -(CH¿2?)m- or formula (II) in which m is an integer of from 3 to 5 and n is 1 or 2, and R?4 and R5¿ are, independently, C¿1? to C5 alkyl; or a N-oxide thereof; or a physiologically-hydrolysable and -acceptable ester of a compound of formula (I) or N-oxide thereof; or a physiologically acceptable acid addition or quaternary ammonium salt of a compound of formula (I), or of an ester or N-oxide thereof.