2-carbethoxy-3,4-dihydro-2H-naphtho[1,2-b]pyran | 169747-40-4

• 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: 2-carbethoxy-3,4-dihydro-2H-naphtho[1,2-b]pyran
• 英文别名: ethyl 3,4-dihydro-2H-benzo[h]chromene-2-carboxylate；ethyl 3,4dihydro-2H-naphto[1,2-b]pyran-2-carboxylate
• CAS: 169747-40-4
• 化学式: C₁₆H₁₆O₃
• 分子量: 256.301
• InChiKey: CJTLQEDMMYPVFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-carbethoxy-3,4-dihydro-2H-naphtho[1,2-b]pyran 在 lithium aluminium tetrahydride 、 potassium hydroxide 作用下， 以 四氢呋喃 、 水 、 异丙醇 为溶剂， 反应 6.0h， 生成 (3,4-dihydro-2H-benzo[h]chromen-2-yl)methanol
  参考文献：
  名称：

  Design and synthesis of 3,4-dihydro-2H-benzo[h]chromene derivatives as potential NF-κB inhibitors

  摘要：

  A novel class of NF-kappa B inhibitors were designed and synthesized based on KL-1156 (6-hydroxy-7-methoxychroman-2-carboxylic acid phenyl amide) which is unambiguously considered to be a promising inhibitor for the translocation step of NF-kappa B. Especially in this study we focused on the modifying the chroman moiety of KL-1156 into four parts for exploring the SAR studies linked with physical properties of substituents resulted the development of novel 1a-k, 2a-f, 3a-d and 4a-d derivatives of 3,4-dihydro-2H-benzo[h] chromene. From the SAR studies we were very delightfully identified that several new N-aryl-3,4-dihydro-2H-benzo[h] chromene-2-carboxamide derivatives (1a-k) exhibited good inhibitory activity and anti-proliferative activity than parent lead compound KL-1156, among them 1i exhibited outstanding inhibitory effect on LPS-induced NF-kappa B transcriptional activity and anti-proliferative activity on NCI-H23 lung cancer cell lines than KL-1156. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.053
• 作为产物：
  描述：

  2-乙酰基-1-萘酚 在 乙醇 、 palladium 10% on activated carbon 、 氢气 、 sodium 作用下， 以 乙醇 为溶剂， 反应 15.0h， 生成 2-carbethoxy-3,4-dihydro-2H-naphtho[1,2-b]pyran
  参考文献：
  名称：

  Design and synthesis of 3,4-dihydro-2H-benzo[h]chromene derivatives as potential NF-κB inhibitors

  摘要：

  A novel class of NF-kappa B inhibitors were designed and synthesized based on KL-1156 (6-hydroxy-7-methoxychroman-2-carboxylic acid phenyl amide) which is unambiguously considered to be a promising inhibitor for the translocation step of NF-kappa B. Especially in this study we focused on the modifying the chroman moiety of KL-1156 into four parts for exploring the SAR studies linked with physical properties of substituents resulted the development of novel 1a-k, 2a-f, 3a-d and 4a-d derivatives of 3,4-dihydro-2H-benzo[h] chromene. From the SAR studies we were very delightfully identified that several new N-aryl-3,4-dihydro-2H-benzo[h] chromene-2-carboxamide derivatives (1a-k) exhibited good inhibitory activity and anti-proliferative activity than parent lead compound KL-1156, among them 1i exhibited outstanding inhibitory effect on LPS-induced NF-kappa B transcriptional activity and anti-proliferative activity on NCI-H23 lung cancer cell lines than KL-1156. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.053

文献信息

• Vasoconstrictive dihydrobenzopyran derivatives
  申请人：Janssen Pharmaceutica, N.V.

  公开号：US05824682A1

  公开（公告）日：1998-10-20

  The present invention is concerned with compounds of formula ##STR1## the pharmaceutically acceptable acid addition salts thereof, and the stereochemically isomeric forms thereof, wherein R.sup.1 is hydrogen or C.sub.1-6 alkyl; R.sup.2 is hydrogen or C.sub.1-6 alkyl; R.sup.3 is hydrogen or C.sub.1-6 alkyl; R.sup.4 is hydrogen, halo, C.sub.1-6 alkyl, hydroxy, C.sub.1-6 alkyloxy, aryloxy or arylmethoxy; R.sup.5 and R.sup.6 designate R.sup.5a and R.sup.6a wherein R.sup.5a and R.sup.6a taken together form a bivalent radical; or R.sup.5 and R.sup.6 can designate R.sup.5b and R.sup.6b wherein R.sup.5b is hydrogen and R.sup.6b is a heterocycle or an optionally substituted alkenyl or alkynyl group; or R.sup.5 and R.sup.6 designate R.sup.5c and R.sup.6c, wherein R.sup.5c and R.sup.6c are hydrogen, halo, C.sub.1-6 alkyl, C.sub.3-6 alkenyl, C.sub.3-6 alkynyl, hydroxy, C.sub.1-6 alkyloxy, cyano, aminoC.sub.1-6 alkyl, carboxyl, C.sub.1-6 alkyloxycarbonyl, nitro, amino, aminocarbonyl, C.sub.1-6 alkylcarbonylamino, or mono-di(C.sub.1-6 alkyl)amino; Q is a heterocyclic ring containing at least one nitrogen atom or a radical of formula ##STR2## pharmaceutical compositions, preparations and use as a medicine are also described.

  本发明涉及式为##STR1##的化合物，其药学上可接受的酸盐，以及其立体异构体，其中R.sup.1是氢或C.sub.1-6烷基；R.sup.2是氢或C.sub.1-6烷基；R.sup.3是氢或C.sub.1-6烷基；R.sup.4是氢，卤素，C.sub.1-6烷基，羟基，C.sub.1-6烷氧基，芳氧基或芳基甲氧基；R.sup.5和R.sup.6指R.sup.5a和R.sup.6a，其中R.sup.5a和R.sup.6a结合形成双价基团；或者R.sup.5和R.sup.6可以指R.sup.5b和R.sup.6b，其中R.sup.5b是氢，R.sup.6b是杂环或可选取代的烯丙基或炔基基团；或者R.sup.5和R.sup.6指R.sup.5c和R.sup.6c，其中R.sup.5c和R.sup.6c是氢，卤素，C.sub.1-6烷基，C.sub.3-6烯基，C.sub.3-6炔基，羟基，C.sub.1-6烷氧基，氰基，氨基C.sub.1-6烷基，羧基，C.sub.1-6烷氧基羰基，硝基，氨基，氨基羰基，C.sub.1-6烷基羰基氨基，或单-二(C.sub.1-6烷基)氨基；Q是含有至少一个氮原子的杂环或式##STR2##的基团，还描述了制药组合物、制剂和作为药物的用途。
• Bondarev, Mikhail; Iwamura, Tatsunori; Hynd, Donna, Medicinal Chemistry Research, 1998, vol. 8, # 6, p. 333 - 342
  作者：Bondarev, Mikhail、Iwamura, Tatsunori、Hynd, Donna、Mazzocco, Lucia、Lee, David K. H.、Dukat, Malgorzata、Glennon, Richard A.

  DOI：——

  日期：——
• Derivatives of 2,2'-iminobisethanol
  申请人：JANSSEN PHARMACEUTICA N.V.

  公开号：EP0145067B1

  公开（公告）日：1989-01-25
• US4654362A
  申请人：——

  公开号：US4654362A

  公开（公告）日：1987-03-31
• Design and synthesis of 3,4-dihydro-2H-benzo[h]chromene derivatives as potential NF-κB inhibitors
  作者：Minho Choi、Young-Sik Hwang、Arepalli Sateesh Kumar、Hyeju Jo、Yeongeun Jeong、Yunju Oh、Joonkwang Lee、Jieun Yun、Youngsoo Kim、Sang-bae Han、Jae-Kyung Jung、Jungsook Cho、Heesoon Lee

  DOI：10.1016/j.bmcl.2014.04.053

  日期：2014.6

  A novel class of NF-kappa B inhibitors were designed and synthesized based on KL-1156 (6-hydroxy-7-methoxychroman-2-carboxylic acid phenyl amide) which is unambiguously considered to be a promising inhibitor for the translocation step of NF-kappa B. Especially in this study we focused on the modifying the chroman moiety of KL-1156 into four parts for exploring the SAR studies linked with physical properties of substituents resulted the development of novel 1a-k, 2a-f, 3a-d and 4a-d derivatives of 3,4-dihydro-2H-benzo[h] chromene. From the SAR studies we were very delightfully identified that several new N-aryl-3,4-dihydro-2H-benzo[h] chromene-2-carboxamide derivatives (1a-k) exhibited good inhibitory activity and anti-proliferative activity than parent lead compound KL-1156, among them 1i exhibited outstanding inhibitory effect on LPS-induced NF-kappa B transcriptional activity and anti-proliferative activity on NCI-H23 lung cancer cell lines than KL-1156. (C) 2014 Elsevier Ltd. All rights reserved.