8-fluoro-5-methoxy-1,2,3,4-tetrahydronaphthalen-1-one | 49800-59-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 8-fluoro-5-methoxy-1,2,3,4-tetrahydronaphthalen-1-one
• 英文别名: 8-fluoro-5-methoxy-3,4-dihydronaphthalen-1(2H)-one；8-fluoro-5-methoxytetralone；8-Fluoro-5-methoxy-3,4-dihydro-2H-1-naphthalenone；8-Fluoro-5-methoxy-1-tetralone；8-fluoro-5-methoxy-3,4-dihydro-2H-naphthalen-1-one
• CAS: 49800-59-1
• 化学式: C₁₁H₁₁FO₂
• mdl: MFCD11518793
• 分子量: 194.206
• InChiKey: UKTORPDEFRENTM-UHFFFAOYSA-N

物化性质

• 沸点：
  330.8±42.0 °C(Predicted)
• 密度：
  1.206±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-fluoro-5-methoxy-1,2,3,4-tetrahydronaphthalen-1-one 在 吡啶 、 盐酸 、 三氯化铝 、 tris(dibenzylideneacetone)dipalladium (0) 、 乙基溴化镁 、 (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl 、 sodium t-butanolate 作用下， 以 乙醚 、 二氯甲烷 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 53.5h， 生成 N-benzyl-N-[4-fluoro-5-(1H-imidazol-4-yl)-7,8-dihydro-1-naphthalenyl]methanesulfonamide
  参考文献：
  名称：

  Synthesis and Structure−Activity Studies on N-[5-(1H-Imidazol-4-yl)-5,6,7,8-tetrahydro-1-naphthalenyl]methanesulfonamide, an Imidazole-Containing α_1A-Adrenoceptor Agonist

  摘要：

  Structure-activity studies were performed on the alpha(1A)-adrenoceptor (AR) selective agonist N-[5-(1H-imidazol-4-yl)-5,6,7,8-tetrahydro-1-naphthalenyl]methanesulfonamide (4). Compounds were evaluated for binding activity at the alpha(1A), alpha(1b), alpha(1d), alpha(2a), and alpha(2B) subtypes. Functional activity in tissues containing the alpha(1A) (rabbit urethra), alpha(1B) (rat spleen), alpha(1D) (rat aorta), and alpha(2A) (rat prostatic vas deferens) was also evaluated. A dog in vivo model simultaneously measuring intraurethral pressure (IUP) and mean arterial pressure (ALAP) was used to assess the uroselectivity of the compounds. Many of the compounds that were highly selective in vitro for the alpha(1A)-AR subtype were also more uroselective in vivo for increasing IUP over MAP than the nonselective alpha(1)-agonists phenylpropanolamine (PPA) (1) and ST-1059 (2, the active metabolite of midodrine), supporting the hypothesis that greater alpha(1A) selectivity would reduce cardiovascular side effects. However, the data also support a prominent role of the alpha(1A)-AR subtype in the control of MAP.

  DOI：

  10.1021/jm030551a
• 作为产物：
  描述：

  Ethyl 4-(5-fluoro-2-methoxyphenyl)-4-oxobutanoate 在 palladium on activated charcoal 高氯酸 、 氢气 作用下， 以 溶剂黄146 为溶剂， 90.0 ℃ 、413.69 kPa 条件下， 反应 0.75h， 生成 8-fluoro-5-methoxy-1,2,3,4-tetrahydronaphthalen-1-one
  参考文献：
  名称：

  Synthesis of 8-fluororhein

  摘要：

  8-Fluoro-5-methoxy-1-tetralone has been formylated. aromatised and alkylated to give 8-fluoro-1-isopropoxy-5-methoxy-2-naphthaldehyde 11. Condensation of this with a phosphonosuccinate gave, after deprotection, the 4-naphthylbutenoic acid which was cyclised and methylated to give the ethyl 9-fluoro-10-isopropoxy-4,6-dimethoxy-2-carboxylate 12. Removal of the isopropyl group, dichromate oxidation and deprotection gave 8-fluorohein 3, an analogue of the osteoarthritis drug rhein.

  DOI：

  10.1039/p19940002131

文献信息

• Pharmaceutical compounds
  申请人：Lilly Industries Limited

  公开号：US05480873A1

  公开（公告）日：1996-01-02

  Pharmaceutical compounds of the formula ##STR1## in which R.sup.1 and R.sup.2 are each hydrogen, hydroxyl, halo, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, acyloxy, --O-glucoside, optionally substituted phenyl or optionally substituted phenyl-C.sub.1-4 alkoxy; R.sup.3 is tetrazolyl, or and R.sup.4 and R.sup.5 are each hydrogen, hydroxy, acyloxy, nitro, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, halo, optionally substituted phenyl, --SO.sub.3 H or --NR'R" where R' and R" are each hydrogen or C.sub.1-4 alkyl; provided that when R.sup.3 is --CR'R".CHR'"CO.sub.2 H or tetrazolyl, R.sup.1 and R.sup.2 are each hydroxyl, halo, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, acyloxy, --O-glucoside, optionally substituted phenyl or optionally substituted phenyl C.sub.1-4 alkoxy; and or a pharmaceutically acceptable salt or ester thereof.

  公式为##STR1##的药物化合物，其中R.sup.1和R.sup.2分别为氢、羟基、卤素、C.sub.1-4烷基、C.sub.1-4烷氧基、酰氧基、-O-葡萄糖苷、可选择取代的苯基或可选择取代的苯基-C.sub.1-4烷氧基；R.sup.3为四唑基，或者R.sup.4和R.sup.5分别为氢、羟基、酰氧基、硝基、C.sub.1-4烷基、C.sub.1-4烷氧基、卤素、可选择取代的苯基、-SO.sub.3 H或-NR'R"，其中R'和R"分别为氢或C.sub.1-4烷基；但是当R.sup.3为--CR'R".CHR'"CO.sub.2 H或四唑基时，R.sup.1和R.sup.2分别为羟基、卤素、C.sub.1-4烷基、C.sub.1-4烷氧基、酰氧基、-O-葡萄糖苷、可选择取代的苯基或可选择取代的苯基-C.sub.1-4烷氧基；或其药学上可接受的盐或酯。
• [EN] PYRIMIDINE DERIVATIVES<br/>[FR] DÉRIVÉS DE PYRIMIDINE
  申请人：IDORSIA PHARMACEUTICALS LTD

  公开号：WO2018210992A1

  公开（公告）日：2018-11-22

  The present invention relates to pyrimidine derivatives of formula (I) wherein (R1)n, R3, R4a, R5b, and Ar1 are as described in the description and their use in the treatment of cancer by modulating an immune response comprising a reactivation of the immune system in the tumor. The invention further relates to novel benzofurane and benzothiophene derivatives of formula (III) and their use as pharmaceuticals, to their preparation, to pharmaceutically acceptable salts thereof, and to their use as pharmaceuticals, to pharmaceutical compositions containing one or more compounds of formula (I), and especially to their use as modulators of the prostaglandin 2 receptors EP2 and/or EP4.

  本发明涉及式(I)的嘧啶衍生物，其中(R1)n，R3，R4a，R5b和Ar1如描述中所述，及其用于通过调节肿瘤中的免疫系统的再激活来治疗癌症的免疫应答。本发明进一步涉及新颖的苯并呋喃和苯并噻吩衍生物式(III)及其作为药物的使用，其制备方法，药用可接受的盐，以及作为药物的使用，包括含有式(I)的一个或多个化合物的药物组合物，尤其是它们作为前列腺素2受体EP2和/或EP4的调节剂的使用。
• 4-Imidazole derivatives of benzyl and restricted benzyl sulfonamides, sulfamides, ureas, carbamates, and amides and their use
  申请人：——

  公开号：US20030073850A1

  公开（公告）日：2003-04-17

  Compounds of formula I 1 are useful in treating diseases prevented by or ameliorated with &agr; 1A agonists. Also disclosed are &agr; 1A agonist compositions and a method of activating &agr; 1 adrenoceptors in a mammal.

  公式I的化合物在治疗由&agr; 1A激动剂预防或改善的疾病中很有用。还公开了&agr; 1A激动剂组合物和在哺乳动物中激活&agr; 1肾上腺素受体的方法。
• Spiro Hydantoin Aldose Reductase Inhibitors
  作者：Reinhard Sarges、Rodney C. Schnur、John L. Belletire、Michael J. Peterson

  DOI：10.1021/jm00396a037

  日期：1988.1

  formation from glucose, catalyzed by the enzyme aldose reductase, is believed to play a role in the development of certain chronic complications of diabetes mellitus. Spiro hydantoins derived from five- and six-membered ketones fused to an aromatic ring or ring system inhibit aldose reductase isolated from calf lens. In vivo these compounds are potent inhibitors of sorbitol formation in sciatic nerves of

  据信由醛糖还原酶催化的葡萄糖形成山梨醇在糖尿病的某些慢性并发症的发生中起作用。源自与芳香族环或环系统融合的五元和六元酮的螺乙内酰脲抑制从小牛晶状体分离的醛糖还原酶。在体内，这些化合物是链脲佐剂化大鼠坐骨神经中山梨醇形成的有效抑制剂。在衍生自6-卤代的2,3-二氢-4H-1-苯并吡喃-4-酮（4-苯并二氢吡喃酮）的螺旋乙内酰脲中可达到最佳的体内活性。在2,4-二氢-6-氟螺[4H-1-苯并吡喃-4,4'-咪唑烷] -2'，5'-二酮中，活性仅存在于4S异构体化合物115（CP-45,634，USAN ：山梨醇）。该化合物目前正用于测试人体，
• Imidazoles and related compounds as &agr;1A agonists
  申请人：Abbott Laboratories

  公开号：US06503935B1

  公开（公告）日：2003-01-07

  Compounds having formula I: are useful in treating diseases prevented by or ameliorated with &agr;1A agonists. Also disclosed are &agr;1A agonist compositions and a method of activating &agr;1 adrenoceptors in a mammal.

  具有化学式I的化合物在治疗由α1A激动剂预防或缓解的疾病中很有用。还公开了α1A激动剂组合物和在哺乳动物中激活α1肾上腺素受体的方法。