5,7-二甲基-3,4-二氢-1H-2-萘酮 | 150331-48-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 中文名称: 5,7-二甲基-3,4-二氢-1H-2-萘酮
• 英文名称: 5,7-dimethyl-2-tetralone
• 英文别名: 5,7-dimethyl-3,4-dihydro-1H-naphthalen-2-one
• CAS: 150331-48-9
• 化学式: C₁₂H₁₄O
• mdl: MFCD11042314
• 分子量: 174.243
• InChiKey: XLLBOUOFVRYIQZ-UHFFFAOYSA-N

物化性质

• 沸点：
  302.2±31.0 °C(Predicted)
• 密度：
  1.054±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5,7-二甲基-3,4-二氢-1H-2-萘酮 在 sodium ethanolate 、 sodium hydride 作用下， 以 乙醇 为溶剂， 反应 22.25h， 生成 3-amino-5,6-dihydro-7,9-dimethylbenzo[f]quinazolin-1(2H)-one
  参考文献：
  名称：

  Benzoquinazoline inhibitors of thymidylate synthase: enzyme inhibitory activity and cytotoxicity of some 3-amino- and 3-methylbenzo[f]quinazolin-1(2H)-ones

  摘要：

  The synthesis and thymidylate synthase (TS) inhibitory activity of a series of simple benzo-[f]-quinazolin-1(2H)-ones are described. Fully aromatic 3-amino compounds with compact lipophilic substituents in the 9-position were found to have I50 values as low as 20 nM on the isolated enzyme, and represent the first examples of potent, folate-based TS inhibitors that completely lack any structural feature corresponding to the (p-aminobenzoyl)glutamate moiety of the cofactor. A number of the compounds also showed moderate growth inhibitory activity against a human colon adenocarcinoma cell line (SW480), with IC50 values as low as 2 muM.

  DOI：

  10.1021/jm00068a004
• 作为产物：
  描述：

  (+/-)-5,7-Dimethyl-1-tetralol 在 硫酸 、 双氧水 、 草酸 作用下， 反应 9.75h， 生成 5,7-二甲基-3,4-二氢-1H-2-萘酮
  参考文献：
  名称：

  Benzoquinazoline inhibitors of thymidylate synthase: enzyme inhibitory activity and cytotoxicity of some 3-amino- and 3-methylbenzo[f]quinazolin-1(2H)-ones

  摘要：

  The synthesis and thymidylate synthase (TS) inhibitory activity of a series of simple benzo-[f]-quinazolin-1(2H)-ones are described. Fully aromatic 3-amino compounds with compact lipophilic substituents in the 9-position were found to have I50 values as low as 20 nM on the isolated enzyme, and represent the first examples of potent, folate-based TS inhibitors that completely lack any structural feature corresponding to the (p-aminobenzoyl)glutamate moiety of the cofactor. A number of the compounds also showed moderate growth inhibitory activity against a human colon adenocarcinoma cell line (SW480), with IC50 values as low as 2 muM.

  DOI：

  10.1021/jm00068a004

文献信息

• A concise method for the synthesis of 2-tetralone by titanium tetrachloride-promoted cyclization of 4-aryl-2-hydroxybutanal diethyl acetal
  作者：Yung-Son Hon、Rammohan Devulapally

  DOI：10.1016/j.tetlet.2009.07.129

  日期：2009.10

  4-Aryl-2-hydroxybutanal diethyl acetal, prepared from the reaction of benzyl Grignard reagent and glycidaldehyde diethyl acetal, was treated with titanium tetrachloride to give 2-tetralone in good yield. This highly efficient transformation involves tandem oxonium formation, intramolecular Friedel–Crafts alkylation, deethoxylation, and tautomerization in the same flask.

  由苄基格氏试剂和缩水甘油醛二乙基缩醛反应制得的4-芳基-2-羟基丁醛二乙基缩醛用四氯化钛处理，以良好的收率得到2-四氢萘酮。这种高效的转化过程包括在同一烧瓶中形成串联的氧鎓，分子内的Friedel-Crafts烷基化反应，脱乙氧基化反应和互变异构反应。
• The First Synthesis of Natural Occurring Juncaceae Coumarin, 9-Hydroxy-8-methyl-3H-benzo[f]chromen-3-one, Featuring a One-pot Rearrangement and Aromatization Cascade
  作者：Yung-Son Hon、Ya-Chun Hong、Bor-Cherng Hong、Ju-Hsiou Liao

  DOI：10.1002/jccs.201100481

  日期：2012.3

  The synthesis of benzocoumarins from β‐tetralones has been achieved via two pathways in the first total synthesis of the Juncaceae natural product, 9‐hydroxy‐8‐methyl‐3H‐benzo[f]chromen‐3‐one, featuring a one‐pot rearrangement and aromatization cascade.

  从β四氢萘酮benzocoumarins的合成已经在第一全合成通过两条途径达到灯心草科天然产物，9-羟基-8-甲基-3- ħ -苯并[ ˚F ]色烯-3-酮，设有一个单锅重排和芳香化级联。
• [EN] IMIDAZOLE COMPOUNDS FOR THE TREATMENT OF NEURODEGENERATIVE DISORDERS<br/>[FR] COMPOSES D'IMIDAZOLE DESTINES AU TRAITEMENT DE TROUBLES NEURODEGENERATIFS
  申请人：PFIZER PROD INC

  公开号：WO2005092864A1

  公开（公告）日：2005-10-06

  The present invention relates to compounds of the Formula (I) wherein R1, R2, R3, R4, R5, R6, R7 and A are as defined. Compounds of the Formula (I) have activity inhibiting production of Aβ-peptide. The invention also relates to pharmaceutical compositions and methods for treating diseases and disorders, for example, neurodegenerative and/or neurological disorders, e.g., Alzheimer’s disease, in a mammal comprising compounds of the Formula (I).

  本发明涉及式(I)的化合物，其中R1、R2、R3、R4、R5、R6、R7和A的定义如上所述。式(I)的化合物具有抑制Aβ肽产生的活性。本发明还涉及制药组合物和治疗疾病和障碍的方法，例如，神经退行性和/或神经系统疾病，例如阿尔茨海默病，在哺乳动物中包括式(I)的化合物。
• [EN] PHARMACEUTICALLY ACTIVE BENZOQUINAZOLINE COMPOUNDS
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：WO1991019700A1

  公开（公告）日：1991-12-26

  (EN) Compounds of formula (I) or salts thereof, wherein the dotted line represents a single or double bond, R1 is alkyl or amino optionally substituted by alkyl, alkanoyl or benzyl group; R2, R3, R4 and R5 are the same or different and each is selected from hydrogen, phenyl, halo, nitro, a group S(O)nR8 wherein n is the integer 0, 1 or 2 and R8 is halo or alkyl or a group NR9R10 wherein R9 and R10 are both hydrogen, a group NR11R12 wherein R11 and R12 are the same or different and each is hydrogen or alkyl, a group OR13 wherein R13 is hydrogen or C1-4 of alkyl optionally substituted by halo; a C1-4 aliphatic group optionally substituted by a group OR14 or NR14R15 wherein R14 and R15 are the same or different and each is hydrogen or alkyl; or two of R2 to R5 are linked together to form a benzo group, or one of R2 to R5 is a group X-Y-R16 wherein X is CH2, NR17, CO or S(O)m and Y is CH2, NR17, O or S(O)m, or X-Y is O, NR17, -CH=CH- or N=N-, are disclosed as pharmacological agents useful in the treatment of tumours. Pharmaceutical compositions and methods for the preparation of compounds of formula (I) are also described.(FR) Composés de formule (I), ou leurs sels, dans laquelle la ligne en pointillés représente une liaison simple ou double, R1 représente alkyle ou amino facultativement remplacé par un groupe alkyle alcanoyle ou benzyle; R2, R3, R4 et R5 sont identiques ou différents et sont choisis chacun parmi hydrogène, phényle, halo, nitro, un groupe S(O)n R8 dans lequel n représente le nombre entier 0, 1 ou 2 et R8 représente halo ou alkyle ou un groupe NR9R10 dans lequel R9 et R10 représentent l'un et l'autre hydrogène, un groupe NR11R12 dans lequel R11 et R12 sont identiques ou différents et représentent chacun hydrogène ou alkyle, un groupe OR13 dans lequel R13 représente hydrogène ou alkyle facultativement remplacé par halo; un groupe aliphatique contenant un à 4 atomes de carbone facultativement remplacé par un groupe OR14 ou NR14R15 dans lequel R14 et R15 sont identiques ou différents et représentent chacun hydrogène ou alkyle; ou deux des éléments compris entre R2 et R5 sont liés ensemble afin de former un groupe benzo ou un des éléments compris entre R2 et R5 représente un groupe X-Y-R16 dans lequel X représente CH2, NR17, CO ou S(O)m et Y représente CH2, NR17, O ou S(O)m, ou X-Y représente O, NR17, -CH=CH- ou N=N-, lesdits composés de l'invention constituant des agents pharmacologiques utiles dans le traitement de tumeurs. L'invention concerne également des compositions pharmaceutiques ainsi que des procédés de préparations de composés de formule (I).

  (I)式化合物或其盐，其中虚线表示单键或双键，R1是烷基或氨基，可选择地被烷基、酰基或苄基取代；R2、R3、R4和R5相同或不同，每个都选自氢、苯基、卤素、硝基、S（O）nR8基团，其中n是整数0、1或2，R8是卤素或烷基或NR9R10基团，其中R9和R10都是氢，或NR11R12基团，其中R11和R12相同或不同，每个是氢或烷基，或OR13基团，其中R13是氢或C1-4烷基，可选择地被卤素取代；C1-4脂肪基，可选择地被OR14或NR14R15基团取代，其中R14和R15相同或不同，每个是氢或烷基；或R2到R5中的两个相互连接形成苯环，或R2到R5中的一个是X-Y-R16基团，其中X是CH2、NR17、CO或S（O）m，Y是CH2、NR17、O或S（O）m，或X-Y是O、NR17、-CH=CH-或N=N-，作为治疗肿瘤的药理学药剂。还描述了制备(I)式化合物的制药组合物和方法。
• Imidazole compounds for the treatment of neurodegenerative disorders
  申请人：Brodney A. Michael

  公开号：US20050215610A1

  公开（公告）日：2005-09-29

  The present invention relates to compounds of the Formula I wherein R 1 , R 2 , R 3 , R 4 , R 6 , R 7 and A are as defined. Compounds of the Formula I have activity inhibiting production of Aβ-peptide. The invention also relates to pharmaceutical compositions and methods for treating diseases and disorders, for example, neurodegenerative and/or neurological disorders, e.g., Alzheimer's disease, in a mammal comprising compounds of the Formula I.

  本发明涉及公式I中的化合物，其中R1、R2、R3、R4、R6、R7和A的定义如所述。公式I的化合物具有抑制Aβ肽生成活性。本发明还涉及制备包含公式I化合物的药物组合物以及治疗哺乳动物的疾病和障碍的方法，例如神经退行性和/或神经系统疾病，例如阿尔茨海默病。