5-Chlor-1,3,3-trimethyl-indolin-2-spiro-3'-<3H>naphtho<2,1-b>pyran | 20200-56-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 5-Chlor-1,3,3-trimethyl-indolin-2-spiro-3'-<3H>naphtho<2,1-b>pyran
• 英文别名: 5'-chloro-1',3',3'-trimethyl-1',3'-dihydro-spiro[benzo[f]chromene-3,2'-indole]；5'-Chloro-1',3',3'-trimethyl-spiro[benzo[f]chromene-3,2'-indoline]；5'-chloro-1',3',3'-trimethylspiro[benzo[f]chromene-3,2'-indole]
• CAS: 20200-56-0
• 化学式: C₂₃H₂₀ClNO
• 分子量: 361.871
• InChiKey: LPHJVWLQTPUTDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  26
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-氯-1,3,3-三甲基-2-亚甲基吲哚啉 、 2-羟基-1-萘甲醛 以 乙醇 为溶剂， 反应 4.0h， 以96%的产率得到5-Chlor-1,3,3-trimethyl-indolin-2-spiro-3'-<3H>naphtho<2,1-b>pyran
  参考文献：
  名称：

  Spirobipyridopyrans, spirobinaphthopyrans, indolinospiropyridopyrans, indolinospironaphthopyrans and indolinospironaphtho-1,4-oxazines: synthesis, study of X-ray crystal structure, antitumoral and antiviral evaluation

  摘要：

  The novel racemic indolinospiroberizopyrans (5-7), indolinospironaphthopyrans (11-14) and indolinospironaphtho-1,4-oxazine (17) were synthesized by an aldol type of condensation of 1',3',3'-trimethyl-2'-methyleneindoline and its 5-substituted derivatives with an appropriately substituted hydroxybenzaldehyde, hydroxynaphthaldehyde or nitrosonaphthol. An unequivocal proof of the stereo structures of 9 and 17 was obtained by the single-crystal X-ray diffraction method. A substituted indoline ring and the benzopyran ring in 9 and the naphtho-1,4-oxazine moiety in 17 are interconnected via the common chiral atom and positioned almost perpendicularly to each other. The five-membered 2,3-dihydropyrrolo moiety of the indoline ring adopts an envelope conformation in both structures. Of all the compounds of this series, spirobipyridopyran (1) inhibited specifically the growth of human melanoma (HBL) (IC50: 0.9 muM) cells but not the growth of normal fibroblasts (WI38). Indolinospirobenzopyrans (8-10) showed significant cytostatic activities against all tumor cell lines. However, these compounds also exhibited a cytotoxic effect on normal human fibroblasts. The indolinospirobenzopyrans 4, 6-8, 10 and the indolinospironaphtho-1,4-oxazine 16 showed, albeit modest, selectivity as antiviral agents against varicella-zoster virus (VZV) and/or cytomegalovirus (CMV) (EC50 Within the concentration range of 1.0-12.6 muM). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.12.010

文献信息

• Hinnen,A. et al., Bulletin de la Societe Chimique de France, 1968, p. 2066 - 2074
  作者：Hinnen,A. et al.

  DOI：——

  日期：——
• US5551973A
  申请人：——

  公开号：US5551973A

  公开（公告）日：1996-09-03
• US5593486A
  申请人：——

  公开号：US5593486A

  公开（公告）日：1997-01-14
• US5633109A
  申请人：——

  公开号：US5633109A

  公开（公告）日：1997-05-27
• Spirobipyridopyrans, spirobinaphthopyrans, indolinospiropyridopyrans, indolinospironaphthopyrans and indolinospironaphtho-1,4-oxazines: synthesis, study of X-ray crystal structure, antitumoral and antiviral evaluation
  作者：Silvana Raić-Malić、Linda Tomašković、Draginja Mrvoš-Sermek、Biserka Prugovečki、Mario Cetina、Mira Grdiša、Krešimir Pavelić、Albrecht Mannschreck、Jan Balzarini、Erik De Clercq、Mladen Mintas

  DOI：10.1016/j.bmc.2003.12.010

  日期：2004.3

  The novel racemic indolinospiroberizopyrans (5-7), indolinospironaphthopyrans (11-14) and indolinospironaphtho-1,4-oxazine (17) were synthesized by an aldol type of condensation of 1',3',3'-trimethyl-2'-methyleneindoline and its 5-substituted derivatives with an appropriately substituted hydroxybenzaldehyde, hydroxynaphthaldehyde or nitrosonaphthol. An unequivocal proof of the stereo structures of 9 and 17 was obtained by the single-crystal X-ray diffraction method. A substituted indoline ring and the benzopyran ring in 9 and the naphtho-1,4-oxazine moiety in 17 are interconnected via the common chiral atom and positioned almost perpendicularly to each other. The five-membered 2,3-dihydropyrrolo moiety of the indoline ring adopts an envelope conformation in both structures. Of all the compounds of this series, spirobipyridopyran (1) inhibited specifically the growth of human melanoma (HBL) (IC50: 0.9 muM) cells but not the growth of normal fibroblasts (WI38). Indolinospirobenzopyrans (8-10) showed significant cytostatic activities against all tumor cell lines. However, these compounds also exhibited a cytotoxic effect on normal human fibroblasts. The indolinospirobenzopyrans 4, 6-8, 10 and the indolinospironaphtho-1,4-oxazine 16 showed, albeit modest, selectivity as antiviral agents against varicella-zoster virus (VZV) and/or cytomegalovirus (CMV) (EC50 Within the concentration range of 1.0-12.6 muM). (C) 2003 Elsevier Ltd. All rights reserved.