3,4-dihydro-2H-benzo[h]chromene-2-carboxylic acid | 99228-18-9

• 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: 3,4-dihydro-2H-benzo[h]chromene-2-carboxylic acid
• 英文别名: 3,4-dihydro-2H-naphtho[1,2-b]pyran-2-carboxylic acid
• CAS: 99228-18-9
• 化学式: C₁₄H₁₂O₃
• 分子量: 228.247
• InChiKey: FHQBGZPPTWKGRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,4-dihydro-2H-benzo[h]chromene-2-carboxylic acid 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 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：

  4-oxo-4H-benzo[h]chromene-2-carboxylic acid 在 钯 作用下， 以 乙二醇甲醚 为溶剂， 以7 parts (61.4%)的产率得到3,4-dihydro-2H-benzo[h]chromene-2-carboxylic acid
  参考文献：
  名称：

  Derivatives of 2,2'-iminobisethanol

  摘要：

  2,2'-亚氨基二乙醇衍生物，具有治疗和/或预防冠状血管系统疾病的有用特性。

  公开号：

  US04654362A1

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。
• VASOCONTRICTIVE DIHYDROBENZOPYRAN DERIVATIVES
  申请人：JANSSEN PHARMACEUTICA N.V.

  公开号：EP0714396A1

  公开（公告）日：1996-06-05
• US4654362A
  申请人：——

  公开号：US4654362A

  公开（公告）日：1987-03-31
• US6100268A
  申请人：——

  公开号：US6100268A

  公开（公告）日：2000-08-08
• [EN] VASOCONTRICTIVE DIHYDROBENZOPYRAN DERIVATIVES<br/>[FR] DERIVES DE DIHYDROBENZOPYRANE VASOCONSTRICTEURS
  申请人：——

  公开号：WO1995005383A1

  公开（公告）日：1995-02-23

  [EN] The present invention is concerned with compounds of formula (I), the pharmaceutically acceptable acid addition salts thereof, and the stereochemically isomeric forms thereof, wherein R<1> is hydrogen or C1-6alkyl; R<2> is hydrogen or C1-6alkyl; R<3> is hydrogen or C1-6alkyl; R<4> is hydrogen, halo, C1-6alkyl, hydroxy, C1-6alkyloxy, aryloxy or arylmethoxy; R<5> and R<6> designate R<5a> and R<6a>, wherein R<5a> and R<6a> taken together form a bivalent radical; or R<5> and R<6> can designate R<5b> and R<6b>, wherein R<5b> is hydrogen and R<6b> is a heterocycle or an optionally substitued alkenyl or alkynyl group; or R<5> and R<6> designate R<5c> and R<6c>, wherein R<5c> and R<6c> are hydrogen, halo, C1-6alkyl, C3-6alkenyl; C3-6alkynyl, hydroxy, C1-6alkyloxy, cyano, aminoC1-6alkyl, carboxyl, C1-6alkyloxycarbonyl, nitro, amino, aminocarbonyl, C1-6alkylcarbonylamino, or mono-di(C1-6alkyl)amino; Q is a heterocyclic ring containing at least one nitrogen atom or a radical of formula (aa), pharmaceutical compositions, preparations and use as a medicine are also described.
  [FR] La présente invention se rapporte à des composés de la formule (I), ainsi qu'à leurs sels d'addition d'acide pharmaceutiquement acceptables et à leurs formes stéréochimiquement isomères; formule dans laquelle R<1> représente hydrogène ou C1-6alkyle; R<2> représente hydrogène ou C1-6alkyle; R<3> représente hydrogène ou C1-6alkyle; R<4> représente hydrogène, halo, C1-6alkyle, hydroxy, C1-6alkyloxy, aryloxy ou arylméthoxy; R<5> et R<6> désignent R<5a> et R6a, lesquels forment ensemble un radical bivalent; ou R<5> et R<6> peuvent désigner R<5b> et R<6b>, R<5b> représentant hydrogène et R<6b> représentant un hétérocycle ou un groupe alcényle ou alcynyle éventuellement substitué; ou R<5> et R<6> désignent R<5c> et R<6c>, lesquels représentent hydrogène, halo, C1-6alkyle, C3-6alcényle, C3-6alcynyle, hydroxy, C1-6alkyloxy, cyano, aminoC1-6alkyle, carboxyle, C1-6alkyloxycarbonyle, nitro, amino, aminocarbonyle, C1-6alkylcarbonylamino ou monodi(C1-6alkyl)amino; Q représente un noyau hétérocyclique contenant au moins un atome d'azote ou un radical de la formule (aa). Des compositions pharmaceutiques, et des procédés de préparation et d'utilisation de ces compositions comme médicaments sont également décrits.