6-羟基-1-萘甲醛 | 571206-45-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 6-羟基-1-萘甲醛
• 英文名称: 6-hydroxy-1-naphthaldehyde
• 英文别名: 6-hydroxynaphthalene-1-carbaldehyde
• CAS: 571206-45-6
• 化学式: C₁₁H₈O₂
• 分子量: 172.183
• InChiKey: BJUBNSLNAGEBDW-UHFFFAOYSA-N

物化性质

• 沸点：
  373.4±15.0 °C(Predicted)
• 密度：
  1.288±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-[2-(piperidin-1-yl)ethoxy]-4'-hydroxybenzophenone 、 6-羟基-1-萘甲醛 在 四氯化钛 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 3.17h， 以66%的产率得到1-(4-hydroxyphenyl)-1-{4-[2-(piperidin-1-yl)ethoxy]phenyl}-2-(6-hydroxynaphthalen-1-yl)ethene
  参考文献：
  名称：

  In vitro evaluation of the anti-estrogenic activity of hydroxyl substituted diphenylnaphthyl alkene ligands for the estrogen receptor☆

  摘要：

  There is still a need for additional scaffolds to further explore tissue selectivity and improving efficacy of selective estrogen receptor modulators (SERMs). A series of hydroxyl substituted diphenylnaphthyl alkene ligands for the two estrogen receptors are described that arose from an initial de novo designed diphenylnaphthyl propylene ligand 1. All compounds gave K(j)s under 10 nM when assayed in the presence of ERalpha. Generally these compounds had very high affinity for both ER isotypes. Moving the hydroxyl group on naphthalene from the 6- to the 5-position of the alpha-naphthalene attached compounds (6b and 6e vs 6c and 6f) had little affect on ER binding nor did altering the position of the naphthalene attachment (alpha or beta) to the alkene moiety. In transfection assays none of the compounds displayed agonistic activity in the absence of E-2. In MCF-7 proliferation assays 6a-d, 6f and 12a-c successfully abrogated E-2 stimulation and resulted in greater than 50% inhibition at 1 muM, a level of efficacy similar to that obtained when the cells were treated with raloxifene. Our results show that this new class of SERMs are good candidates for further study as therapeutic agents for the treatment of breast cancer and osteoporosis. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.11.051
• 作为产物：
  描述：

  6-甲氧基-1-萘甲醛 在 乙硫醇钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 以39%的产率得到6-羟基-1-萘甲醛
  参考文献：
  名称：

  In vitro evaluation of the anti-estrogenic activity of hydroxyl substituted diphenylnaphthyl alkene ligands for the estrogen receptor☆

  摘要：

  There is still a need for additional scaffolds to further explore tissue selectivity and improving efficacy of selective estrogen receptor modulators (SERMs). A series of hydroxyl substituted diphenylnaphthyl alkene ligands for the two estrogen receptors are described that arose from an initial de novo designed diphenylnaphthyl propylene ligand 1. All compounds gave K(j)s under 10 nM when assayed in the presence of ERalpha. Generally these compounds had very high affinity for both ER isotypes. Moving the hydroxyl group on naphthalene from the 6- to the 5-position of the alpha-naphthalene attached compounds (6b and 6e vs 6c and 6f) had little affect on ER binding nor did altering the position of the naphthalene attachment (alpha or beta) to the alkene moiety. In transfection assays none of the compounds displayed agonistic activity in the absence of E-2. In MCF-7 proliferation assays 6a-d, 6f and 12a-c successfully abrogated E-2 stimulation and resulted in greater than 50% inhibition at 1 muM, a level of efficacy similar to that obtained when the cells were treated with raloxifene. Our results show that this new class of SERMs are good candidates for further study as therapeutic agents for the treatment of breast cancer and osteoporosis. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.11.051

文献信息

• Integrin receptor inhibitors
  申请人：GENENTECH, INC.

  公开号：US20020035104A1

  公开（公告）日：2002-03-21

  Provided are compounds of formula (I) 1 wherein A, Q, W, X, Y, Z, R 1 to R 4 , m and n are as defined herein. Compounds of the invention bind to &agr; 4 integrin receptors and thereby inhibit binding of ligands for &agr; 4 integrins which is useful for prophylactic and/or therapeutic treatment of diseases and conditions associated with &agr; 4 integrins or their ligands.

  提供的是式(I)1的化合物，其中A、Q、W、X、Y、Z、R1至R4、m和n的定义如本文所述。本发明的化合物结合到α4整合素受体，从而抑制α4整合素的配体结合，这对于预防和/或治疗与α4整合素或其配体相关的疾病和症状是有用的。
• Biocatalytic reduction of α,β-unsaturated carboxylic acids to allylic alcohols
  作者：Godwin A. Aleku、George W. Roberts、David Leys

  DOI：10.1039/d0gc00867b

  日期：——

  enable reduction of α,β-unsaturated carboxylic acids to allylic alcohols and their saturated analogues. These compounds are prevalent scaffolds in many industrial chemicals and pharmaceuticals. A substrate profiling study of a carboxylic acid reductase (CAR) investigating unexplored substrate space, such as benzo-fused (hetero)aromatic carboxylic acids and α,β-unsaturated carboxylic acids, revealed broad

  我们已经开发了强大的体内和体外生物催化系统，能够将α，β-不饱和羧酸还原为烯丙基醇及其饱和类似物。这些化合物是许多工业化学品和制药中的普遍支架。对羧酸还原酶（CAR）的底物谱研究研究未开发的底物空间，例如苯并稠合的（杂）芳族羧酸和α，β-不饱和羧酸，揭示了广泛的底物耐受性，并提供了有关这些底物的反应模式的信息基材。大肠杆菌表达异源CAR的细胞被用作多步氢化催化剂，以将多种α，β-不饱和羧酸转化为相应的饱和伯醇，转化率高达99％以上。大肠杆菌内源性乙醇脱氢酶（ADH）的广泛底物范围以及大肠杆菌细胞出乎意料的C C键还原活性支持了这一点。另外，重组的大肠杆菌细胞将各种苯并稠合的（杂）芳族羧酸转化为相应的伯醇。另一种单罐体外由CAR和葡萄糖脱氢酶（GDH）组成的两酶系统显示了GDH对各种不饱和醛的混杂羰基还原酶活性。因此，将CAR与GDH驱动的NADP（H）回收系统耦合，可从母体羧酸盐中获得多种
• Design, Synthesis and Various Bioactivity of Acylhydrazone-Containing Matrine Analogues
  作者：Wanjun Ni、Hongjian Song、Lizhong Wang、Yuxiu Liu、Qingmin Wang

  DOI：10.3390/molecules28104163

  日期：——

  Compounds with acylhydrazone fragments contain amide and imine groups that can act as electron donors and acceptors, so they are easier to bind to biological targets and thus generally exhibit significant biological activity. In this work, acylhydrazone fragments were introduced to the C-14 or C-11 position of matrine, a natural alkaloid, aiming to enhance their biological activities. The result of this bioassay showed that many synthesized compounds exhibited excellent anti-virus activity against the tobacco mosaic virus (TMV). Seventeen out of 25 14-acylhydrazone matrine derivatives and 17 out of 20 11-butanehydrazone matrine derivatives had a higher inhibitory activity against TMV than the commercial antiviral agent Ribavirin (the in vitro activity, in vivo inactivation, curative and protection activities at 500 µg/mL were 40.9, 36.5 ± 0.9, 38.0 ± 1.6 and 35.1 ± 2.2%, respectively), and four 11-butanehydrazone matrine derivatives even had similar to or higher activity than the most efficient antiviral agent Ningnanmycin (55.4, 57.8 ± 1.4, 55.3 ± 0.5 and 60.3 ± 1.2% at 500 µg/mL for the above four test modes). Among them, the N-benzyl-11-butanehydrazone of matrine formed with 4-bromoindole-3-carboxaldehyde exhibited the best anti-TMV activity (65.8, 71.8 ± 2.8, 66.8 ± 1.3 and 69.5 ± 3.1% at 500 µg/mL; 29, 33.5 ± 0.7, 24.1 ± 0.2 and 30.3 ± 0.6% at 100 µg/mL for the above four test modes), deserving further investigation as an antiviral agent. Other than these, the two series of acylhydrazone-containing matrine derivatives were evaluated for their insecticidal and fungicidal activities. Several compounds were found to have good insecticidal activities against diamondback moth (Plutella xylostella) and mosquito larvae (Culex pipiens pallens), showing broad biological activities.

  带有酰基腙片段的化合物含有酰胺基和亚胺基，可以充当电子供体和受体，因此更容易与生物靶标结合，通常具有显著的生物活性。在这项研究中，我们在天然生物碱马钱子碱的 C-14 或 C-11 位置引入了酰基腙片段，旨在提高它们的生物活性。生物测定结果表明，合成的许多化合物对烟草花叶病毒（TMV）具有很好的抗病毒活性。在 25 个 14-酰腙马钱子碱衍生物和 20 个 11-丁腙马钱子碱衍生物中，有 17 个对烟草花叶病毒的抑制活性高于商业抗病毒药物利巴韦林（在 500 µg/mL 的浓度下，其体外活性、体内灭活活性、治疗活性和保护活性分别为 40.9、36.5 ± 0.5 ± 0.5）。9、36.5 ± 0.9、38.0 ± 1.6 和 35.1 ± 2.2%），4 个 11-丁烷腙马钱子碱衍生物的活性甚至与最有效的抗病毒药物宁南霉素相近或更高（在 500 µg/mL 时，上述 4 种试验模式的活性分别为 55.4、57.8 ± 1.4、55.3 ± 0.5 和 60.3 ± 1.2%）。其中，与 4-溴吲哚-3-甲醛形成的 N-苄基-11-丁烷腙表现出最佳的抗 TMV 活性（在 500 µg/mL 时分别为 65.8、71.8 ± 2.8、66.8 ± 1.3 和 69.5 ± 3.1%；在 100 µg/mL 时分别为 29、33.5 ± 0.7、24.1 ± 0.2 和 30.3 ± 0.6%，用于上述四种测试模式），值得作为抗病毒剂进一步研究。除此以外，还评估了两个含酰基肼的马钱子碱衍生物系列的杀虫和杀真菌活性。研究发现，一些化合物对菱纹夜蛾（Plutella xylostella）和蚊子幼虫（Culex pipiens pallens）具有良好的杀虫活性，显示出广泛的生物活性。
• A composition for increasing the anti-cancer activity of an anti-cancer compound
  申请人：OTSUKA PHARMACEUTICAL CO., LTD.

  公开号：EP0180188A2

  公开（公告）日：1986-05-07

  A composition for increasing the anti-cancer activity of an anti-cancer compound selected from among 5-fluorouracil and a compound capable of producing 5-fluorouracil in vivo, the composition comprising an effective amount of a pyridine derivative represented by the formula wherein R1 is hydroxy or acyloxy, R2 and R4 are each hydrogen, halogen, amino, carboxyl, carbamoyl, cyano, nitro, lower alkyl, lower alkenyl or lower alkoxycarbonyl, R3 and R are each hydrogen, hydroxy or acyloxy; when at least one of R1, R3 and R5 is hydroxy, the structure of 1-position on the pyridine rina can be duetothe due to the keto-enol tautomerism, said hydrogen attached to nitrogen being optionally substituted with a substituent selected from the group consisting of lower alkyl, tetrahydrofuranyl, tetrahydropyranyl, lower alkoxy-lower alkyl, phthalidyl, carbamoyl, lower alkoxycarbonyl-lower alkylcarbamoyl, phenyl-lower alkoxy-lower alkyl, phenylcarbamoyl which may have a substituent on the phenyl ring, lower alkylcarbamoyl, carboxy-lower alkylcarbamoyl, lower alkylthio-lower alkyl and lower alkenyl, provided that the compound having the following formula is excluded, wherein a is hydrogen, lower alkyl, tetrahydrofuranyl, tetrahydropyranyl, lower alkoxy-lower alkyl, lower alkylcarbamoyl, lower alkylthio-lower alkyl or lower alkenyl.

  一种提高选自5-氟尿嘧啶和一种能在体内产生5-氟尿嘧啶的化合物的抗癌活性的组合物，该组合物包括有效量的由式表示的吡啶衍生物 其中 R1 是羟基或酰氧基，R2 和 R4 分别是氢、卤素、氨基、羧基、氨基甲酰基、氰基、硝基、低级烷基、低级烯基或低级烷氧基羰基，R3 和 R 分别是氢、羟基或酰氧基；当 R1、R3 和 R5 中至少有一个是羟基时，吡啶里纳上 1 位的结构可以是 当 R1、R3 和 R5 中至少有一个是羟基时，吡啶里纳上 1 位的结构可以是酮烯醇同分异构，所述连接到氮上的氢可选择被选自低烷基、四氢呋喃基、四氢吡喃基、低烷氧基低烷基、邻苯二甲酰基、氨基甲酰基、低烷氧基羰基低烷基氨基甲酰基组成的取代基取代、苯基-低级烷氧基-低级烷基、苯基氨基甲酰基（苯基环上可能有取代基）、低级烷基氨基甲酰基、羧基-低级烷基氨基甲酰基、低级烷硫基-低级烷基和低级烯基，但具有下式的化合物除外、 其中 a 为氢、低级烷基、四氢呋喃基、四氢呋喃基、低级烷氧基低级烷基、低级烷基氨基甲酰基、低级烷硫基低级烷基或低级烯基。
• Thermotropic liquid-crystalline aromatic copolymers
  申请人：ENICHEM S.p.A.

  公开号：EP0375036A1

  公开（公告）日：1990-06-27

  Liquid-crystalline, completely aromatic copolyesters are disclosed, which are endowed with a heat stability not lower than 350° C, and are constituted by a succession of repeatitive units containing: wherein A and B, which can be either equal to, or different, from, each other, can be either -O- or -CO- and one of the following moieties: in which Ar can be 1,4-phenylene, 2-monosubstituted-1,4-­phenylene or 4,4′-diphenylene. Also copolyesters also containing amidic bonding groups are disclosed.

  本发明公开了液晶型完全芳香族共聚聚酯，其热稳定性不低于 350°C，由连续的重复单元构成，这些重复单元包含： 其中，A 和 B 可以相互等同或不同，可以是 -O- 或 -CO- 以及下列分子之一： 其中 Ar 可以是 1,4-亚苯基、2-单取代-1,4-亚苯基或 4,4′-二亚苯基。 此外，还公开了同样含有酰胺键基团的共聚多酯。