(R)-α-(1,3-Benzodioxol-5-yl)benzeneethanamine | 170688-18-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (R)-α-(1,3-Benzodioxol-5-yl)benzeneethanamine
• 英文别名: (R) α-(1,3-benzodioxol-5-yl)benzeneethanamine；(R)-alpha-(1,3-benzodioxol-5-yl)benzeneethanamine；(1R)-1-(1,3-benzodioxol-5-yl)-2-phenylethanamine
• CAS: 170688-18-3
• 化学式: C₁₅H₁₅NO₂
• 分子量: 241.29
• InChiKey: XXUGGVBVWGFUDI-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-α-(1,3-Benzodioxol-5-yl)benzeneethanamine 在 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 N-{5-[(R)-2-((R)-1-Benzo[1,3]dioxol-5-yl-2-phenyl-ethylamino)-1-hydroxy-ethyl]-2-benzyloxy-phenyl}-methanesulfonamide
  参考文献：
  名称：

  BMS-196085: A potent and selective full agonist of the human β3 adrenergic receptor

  摘要：

  A series of 4-hydroxy-3-methylsulfonanilido-1,2-diarylethylamines were prepared and evaluated for their human beta (3) adrenergic receptor agonist activity. SAR studies led to the identification of BMS-196085 (25), a potent beta (3) full agonist (K-i = 21 nM, 95% activation) with partial agonist (45%) activity at the beta (1) receptor. Based on its desirable in vitro and in vivo properties, BMS-196085 was chosen for clinical evaluation. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00629-1
• 作为产物：
  描述：

  (R)-2-((R)-1-Benzo[1,3]dioxol-5-yl-2-phenyl-ethylamino)-2-phenyl-ethanol 在 lead(IV) acetate 、 盐酸 作用下， 以 甲醇 为溶剂， 生成 (R)-α-(1,3-Benzodioxol-5-yl)benzeneethanamine
  参考文献：
  名称：

  BMS-196085: A potent and selective full agonist of the human β3 adrenergic receptor

  摘要：

  A series of 4-hydroxy-3-methylsulfonanilido-1,2-diarylethylamines were prepared and evaluated for their human beta (3) adrenergic receptor agonist activity. SAR studies led to the identification of BMS-196085 (25), a potent beta (3) full agonist (K-i = 21 nM, 95% activation) with partial agonist (45%) activity at the beta (1) receptor. Based on its desirable in vitro and in vivo properties, BMS-196085 was chosen for clinical evaluation. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00629-1

文献信息

• Catecholamine surrogates useful as .beta..sub.3 agonists
  申请人：Bristol-Myers Squibb Company

  公开号：US05776983A1

  公开（公告）日：1998-07-07

  Compounds of the formula ##STR1## or pharmaceutically acceptable salts thereof wherein: A is a bond, --(CH.sub.2).sub.n -- or --CH(B)--, where n is an integer of 1 to 3 and B is --CN, --CON(R.sup.9)R.sup.9' or --CO.sub.2 R.sup.7 ; R.sup.1 is lower alkyl, aryl or arylalkyl; R.sup.2 is hydrogen, hydroxy, alkoxy, --CH.sub.2 OH, cyano, --C(O)OR.sup.7, --CO.sub.2 H, --CONH.sub.2, tetrazole, --CH.sub.2 NH.sub.2 or halogen; ##STR2## R.sup.3 is hydrogen, alkyl, heterocycle or R.sup.4 is hydrogen, alkyl or B; R.sup.5, R.sup.5', R.sup.8, R.sup.8' or R.sup.8" are independently hydrogen, alkoxy, lower alkyl, halogen, --OH, --CN, --(CH.sub.2).sub.n NR.sup.6 COR.sup.7, --CON(R.sup.6)R.sup.6', --CON(R.sup.6)OR.sup.6', --CO.sub.2 R.sup.6, --SR.sup.7, --SOR.sup.7, --SO.sub.2 R.sup.7, --N(R.sup.6)SO.sub.2 R.sup.1, --N(R.sup.6)R.sup.6', --NR.sup.6 COR.sup.7, --OCH.sub.2 CON(R.sup.6)R.sup.6', --OCH.sub.2 CO.sub.2 R.sup.7 or aryl; or R.sup.5 and R.sup.5' or R.sup.8 and R.sup.8' may together with the carbon atoms to which they are attached form an aryl or heterocycle; R.sup.6 and R.sup.6' are independently hydrogen or lower alkyl; and R.sup.7 is lower alkyl; R.sup.9 is hydrogen, lower alkyl, alkyl, cycloalkyl, arylalkyl, aryl, heteroaryl; or R.sup.9 and R.sup.9' may together with the nitrogen atom to which they are attached form a heterocycle; with the proviso that when A is a bond or --(CH.sub.2).sub.n and R.sup.3 is hydrogen or unsubstituted alkyl, then R.sup.4 is B or substituted alkyl. These compounds are beta.sub.3 adrenergic receptor agonists and are useful, therefore for example, in the treatment of diabetes, obesity and gastrointestinal diseases.

  化合物的结构式为##STR1##或其药学上可接受的盐，其中：A是一个键，--(CH.sub.2).sub.n--或--CH(B)--，其中n是1到3的整数，B是--CN，--CON(R.sup.9)R.sup.9'或--CO.sub.2R.sup.7; R.sup.1是低碳基，芳香基或芳基烷基; R.sup.2是氢，羟基，烷氧基，--CH.sub.2OH，氰基，--C(O)OR.sup.7，--CO.sub.2H，--CONH.sub.2，四唑，--CH.sub.2NH.sub.2或卤素; ##STR2## R.sup.3是氢，烷基，杂环或R.sup.4是氢，烷基或B; R.sup.5，R.sup.5'，R.sup.8，R.sup.8'或R.sup.8"独立地是氢，烷氧基，低碳基，卤素，--OH，--CN，--(CH.sub.2).sub.nNR.sup.6COR.sup.7，--CON(R.sup.6)R.sup.6'，--CON(R.sup.6)OR.sup.6'，--CO.sub.2R.sup.6，--SR.sup.7，--SOR.sup.7，--SO.sub.2R.sup.7，--N(R.sup.6)SO.sub.2R.sup.1，--N(R.sup.6)R.sup.6'，--NR.sup.6COR.sup.7，--OCH.sub.2CON(R.sup.6)R.sup.6'，--OCH.sub.2CO.sub.2R.sup.7或芳香基; 或R.sup.5和R.sup.5'或R.sup.8和R.sup.8'可以与它们连接的碳原子一起形成一个芳香基或杂环; R.sup.6和R.sup.6'独立地是氢或低碳基; R.sup.7是低碳基; R.sup.9是氢，低碳基，烷基，环烷基，芳基烷基，芳香基，杂芳基; 或R.sup.9和R.sup.9'可以与它们连接的氮原子一起形成一个杂环; 假设当A是键或--(CH.sub.2).sub.n时，R.sup.3是氢或未取代的烷基，则R.sup.4是B或取代的烷基。这些化合物是beta.sub.3肾上腺素受体激动剂，因此在糖尿病，肥胖症和胃肠疾病的治疗中有用。
• Catecholamine surrogates useful as B3 agonists
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：EP0659737A2

  公开（公告）日：1995-06-28

  Compounds of the formula or pharmaceutically acceptable salts thereof wherein: A is a bond, -(CH2)n- or -CH(B)-, where n is an integer of 1 to 3 and B is -CN, -CON(R9)R9' or -C02R7; R1 is lower alkyl, aryl or arylalkyl; R2 is hydrogen, hydroxy, alkoxy, -CH20H, cyano, -C(O)OR7 , -C02H, -CONH2, tetrazole, -CH2NH2 or halogen; R3 is hydrogen, alkyl, heterocycle or R4 is hydrogen, alkyl or B; R5, R5', R8, R8' or R8'' are independently hydrogen, alkoxy, lower alkyl, halogen, -OH, -CN, -(CH2)-nNR6COR7, -CON(R6)R6', -CON(R6)OR6', -C02R6, -SR7, -SOR7, -S02R7, -N(R6)SO2R1, -N(R6)R6', -NR6COR7, -OCH2CON(R6)R6', -OCH2CO2R7 or aryl; or R5 and R5' or R8 and R8' may together with the carbon atoms to which they are attached form an aryl or heterocycle; R6 and R6' are independently hydrogen or lower alkyl; and R7 is lower alkyl; R9 is hydrogen, lower alkyl, alkyl, cycloalkyl, arylalkyl, aryl, heteroaryl; or R9 and R9' may together with the nitrogen atom to which they are attached form a hetocycle; with the proviso that when A is a bond or -(CH2)n and R3 is hydrogen or unsubstituted alkyl, then R4 is B or substituted alkyl. These compounds are beta3 adrenergic receptor agonists and are useful, therefore for example, in the treatment of diabetes, obesity and gastrointestinal diseases.

  式中的化合物 或其药学上可接受的盐类，其中 A 是键、-(CH2)n- 或 -CH(B)-，其中 n 是 1 至 3 的整数，B 是 -CN、-CON(R9)R9' 或 -C02R7； R1 是低级烷基、芳基或芳烷基； R2 是氢、羟基、烷氧基、- 0H、氰基、-C(O)OR7、-C02H、-CONH2、四唑、- NH2 或卤素； R3 是氢、烷基、杂环或卤素。 R4 是氢、烷基或 B； R5、R5'、R8、R8' 或 R8'' 独立地为氢、烷氧基、低级烷基、卤素、-OH、-CN、-( )-nNR6COR7、-CON(R6)R6'、-C02R6、-SR7、-SOR7、-S02R7、-N(R6)SO2R1、-N(R6)R6'、-NR6COR7、-O CON(R6)R6'、-O CO2R7 或芳基；或 R5 和 R5' 或 R8 和 R8'可与它们所连接的碳原子一起形成芳基或杂环； R6 和 R6'独立地为氢或低级烷基；以及 R7 是低级烷基； R9是氢、低级烷基、烷基、环烷基、芳烷基、芳基、杂芳基；或 R9和R9'可与它们所连接的氮原子一起形成一个杂环；但当A是键或-( )n且R3是氢或未取代的烷基时，则R4是B或取代的烷基。这些化合物是β3肾上腺素能受体激动剂，因此可用于治疗糖尿病、肥胖症和胃肠道疾病等。
• Aryloxypropanolamine beta 3 adrenergic agonists
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：EP0714883A1

  公开（公告）日：1996-06-05

  Compounds of the formula I and pharmaceutically acceptable salts thereof wherein:    R1 to R9 are as defined herein and m is the integer 0 or 1. These compounds are beta 3 adrenergic receptor agonists and are useful, therefore for example, in the treatment of diabetes, obesity, gastrointestinal diseases and achalasia.

  式 I 的化合物 及其药学上可接受的盐 其中 R1 至 R9 如本文所定义，m 为整数 0 或 1。这些化合物是β3肾上腺素能受体激动剂，因此可用于治疗糖尿病、肥胖症、胃肠道疾病和贲门失弛缓症等。
• Catecholamine surrogates useful as beta 3 agonists
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：EP0659737B1

  公开（公告）日：2003-03-26
• US5541204A
  申请人：——

  公开号：US5541204A

  公开（公告）日：1996-07-30