(E)-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-but-2-en-1-ol | 161916-81-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (E)-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-but-2-en-1-ol
• 英文别名: (2E)-3-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-2-butenol；(E)-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthalenyl)-2-buten-1-ol；(E)-3-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)but-2-en-1-ol
• CAS: 161916-81-0
• 化学式: C₁₈H₂₆O
• 分子量: 258.404
• InChiKey: LCICCPOYRCXFMX-MDWZMJQESA-N

物化性质

• 沸点：
  383.0±42.0 °C(Predicted)
• 密度：
  0.951±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-but-2-en-1-ol 在 lithium hydroxide 、 三氢化钐 、 正丁基锂 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 生成
  参考文献：
  名称：

  Synthesis of highly potent RXR-specific retinoids: The use of a cyclopropyl group as a double bond isostere

  摘要：

  Retinoids act through two distinct hormonal pathways activated by RAR and RXR ligands. We describe the synthesis of C9-C10 locked retinoid analogs, including the most potent RXR - specific agonist known to date (Compound 5), and discuss the structural features that lead to this specificity.

  DOI：

  10.1016/0960-894x(95)00588-k
• 作为产物：
  描述：

  (E)-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-but-2-enoic acid ethyl ester 在 二异丁基氢化铝 作用下， 生成 (E)-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-but-2-en-1-ol
  参考文献：
  名称：

  Synthesis of highly potent RXR-specific retinoids: The use of a cyclopropyl group as a double bond isostere

  摘要：

  Retinoids act through two distinct hormonal pathways activated by RAR and RXR ligands. We describe the synthesis of C9-C10 locked retinoid analogs, including the most potent RXR - specific agonist known to date (Compound 5), and discuss the structural features that lead to this specificity.

  DOI：

  10.1016/0960-894x(95)00588-k

文献信息

• Fused ring compounds, process for producing the same and use thereof
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US06420375B1

  公开（公告）日：2002-07-16

  To provide a novel compound of the formula: [wherein A1 ix a 5 or 6-membered ring which may be substituted by a group not containing a cyclic group, A2 is an aromatic ring which may be substituted, X is a divalent group, Y is a nitrogen atom or a methine group, Z is an ethenylene which may be substituted or ethynylene, R is a heterocyclic group which may be substituted, provided that 3,4-dihydro-6-[3-(1H-imidazol-1-yl)-1-propenyl]-2(1H)-quinolone and 2-[3-[5-ethyl-6-methyl-2-(benzyloxy)-3-pyridyl]-1-propenyl]benzoxazole are excluded.], or a salt thereof which has steroid C17,20-lyase inhibitory activity, and is useful for preventing and treating mammals suffering from, for example, primary cancer of malignant tumor, its metastasis and recurrence thereof.

  提供一种新颖的化合物，其化学式为： 其中A1是一个5或6成员环，可以被不含环状基团的基团取代，A2是一个芳香环，可以被取代，X是一个二价基团，Y是一个氮原子或一个亚甲基基团，Z是一个可以被取代的乙烯基或乙炔基，R是一个可以被取代的杂环基团，但不包括3,4-二氢-6-[3-(1H-咪唑-1-基)-1-丙烯基]-2(1H)-喹啉和2-[3-[5-乙基-6-甲基-2-(苄氧基)-3-吡啶基]-1-丙烯基]苯并噁唑，或其盐，具有类固醇C17,20-裂解酶抑制活性，对于预防和治疗患有原发性癌症、恶性肿瘤、其转移和复发等疾病的哺乳动物是有用的。
• Retinoic acid X-receptor ligands
  申请人：Hoffmann-La Roche Inc.

  公开号：US05801253A1

  公开（公告）日：1998-09-01

  Compounds of formula (I) wherein R.sup.1 -R.sup.7, R.sup.10, X and the dotted bond have the meaning given in the specification, bind selectively to retinoid RXR receptors and are useful as antiproliferative agents for dermatological and oncological indications.

  式（I）中的化合物，其中R.sup.1 -R.sup.7，R.sup.10，X和点线键具有规范中给定的含义，可选择性地结合到视黄醇RXR受体，并可用作皮肤病和肿瘤学适应症的抗增殖剂。
• Alicyclic phospholipase A.sub.2 inhibitors
  申请人：Bristol-Myers Squibb Company

  公开号：US05436369A1

  公开（公告）日：1995-07-25

  Certain novel alicyclic compounds are effective phospholipase A.sub.2 (PLA.sub.2) inhibitors.

  某些新型脂环化合物是有效的磷脂酶A.sub.2（PLA.sub.2）抑制剂。
• 2,4-pentadienoic acid derivatives having retinoid-like biological activity
  申请人：Allergan Sales, Inc.

  公开号：US20020082419A1

  公开（公告）日：2002-06-27

  Compounds of Formula 1 1 wherein Z is selected from the group consisting of the radicals shown in Formula 2 and in Formula 3, 2 Y is cycloalkyl or cycloalkenyl of 3 to 8 carbons optionally substituted with one or two R 4 groups, or Y is selected from phenyl, pyridyl, thienyl, furyl, pyrrolyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl, oxazolyl, and imidazolyl, said groups being optionally substituted with one or two R 4 groups, the divalent Y radical being substituted by the Z and —CR 1 ═CR 1 —CR 1 ═CR 1 groups on adjacent carbons; X is S, O, or NR 5 ; n is 1 or 2; R 1 and R 2 independently are H, lower alkyl or fluoroalkyl; R 3 is hydrogen, lower alkyl, Cl or Br; R 4 is lower alkyl, fluoroalkyl or halogen; R 5 is H or lower alkyl, and B is hydrogen, COOH or a pharmaceutically acceptable salt thereof, COOR 8 , CONR 9 R 10 , —CH 2 OH, CH 2 OR 11 , CH 2 OCOR 11 , CHO, CH(OR 12 ) 2 , CHOR 13 O, —COR 7 , CR 7 (OR 12 ) 2 , CR 7 OR 13 O, or tri-lower alkylsilyl, where R 7 is an alkyl, cycloalkyl or alkenyl group containing 1 to 5 carbons, R 8 is an alkyl group of 1 to 10 carbons, a cycloalkyl group of 5 to 10 carbons or trimethylsilylalkyl where the alkyl group has 1 to 10 carbons, or R 8 is phenyl or lower alkylphenyl, R 9 and R 10 independently are hydrogen, an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5-10 carbons, or phenyl or lower alkylphenyl, R 11 is lower alkyl, phenyl or lower alkylphenyl, R 12 is lower alkyl, and R 13 is divalent alkyl radical of 2-5 carbons, have retinoid like biological activity.

  化合物的化学式为11，其中Z选择自式2和式3中所示的基团组成的群体，2Y为3至8个碳原子的环烷基或环烯基，可选地带有一个或两个R4基团，或者Y选择自苯基、吡啶基、噻吩基、呋喃基、吡咯基、吡嗪基、嘧啶基、吡嗪啉基、噻唑基、噁唑基和咪唑基，所述基团可选地带有一个或两个R4基团，双价的Y基团被相邻碳原子上的Z和—CR1═CR1—CR1═CR1基团所取代；X为S、O或NR5；n为1或2；R1和R2独立地为H、低碳基或氟碳基；R3为氢、低碳基、Cl或Br；R4为低碳基、氟碳基或卤素；R5为H或低碳基；B为氢、COOH或其药学上可接受的盐、COOR8、CONR9R10、—CH2OH、CH2OR11、CH2OCOR11、CHO、CH(OR12)2、CHOR13O、—COR7、CR7(OR12)2、CR7OR13O或三个低碳基硅烷基，其中R7为含1至5个碳原子的烷基、环烷基或烯基，R8为1至10个碳原子的烷基、5至10个碳原子的环烷基或三甲基硅基烷基，其中烷基含有1至10个碳原子，或者R8为苯基或低碳基苯基，R9和R10独立地为氢、1至10个碳原子的烷基、5-10个碳原子的环烷基或苯基或低碳基苯基，R11为低碳基、苯基或低碳基苯基，R12为低碳基，R13为2-5个碳原子的双价烷基基团，具有类视黄醛生物活性。
• Alicyclic phospholipase A2 inhibitors
  申请人：Bristol-Myers Company

  公开号：EP0629604A2

  公开（公告）日：1994-12-21

  Compounds of Formula I: wherein the bonds between C₂ and C3 and/or between C₄ and C₅ are unsaturated; X = COOH, H, F, Cl, Br, I, COOR'', CONH₂, COR''', CHO, CH₂OH, CH₂OR''', OH, OR''', CF₃, C1-6 alkyl, C1-6 alkenyl, C1-6 haloalkyl, NO₂, P(O)(OH)₂, SO₂H, or SO₃H; R = substituted or unsubstituted alkyl, aryl, arylalkyl, alkenyl, or arylalkenyl groups, with the proviso that each of these groups must have 6 or more carbons (preferably 6 to 30) and R cannot be R' = H or C1-6 alkyl; R'' = H, C1-6 alkyl, C(R³)₂OC(O)R⁴, CH₂CH₂NR⁵R⁶, CH₂CH₂CH₂NR⁵R⁶, CH₂C(O)N(R⁶)₂, or other groups yielding physiologically hydrolyzable esters; R''' = C1-6 alkyl; R³ = H, CH₃, C₂H₅, CH₃CH₂CH₂ (with R³'s being the same or different); R⁴ = C6-12 aryl, C1-7 linear, branched or cyclic alkyl, or C1-7 linear, branched or cyclic alkoxy; R⁵ = R⁶, or when linked with R⁶, is a C₃-C₆ cycloalkyl or a -CH₂CH₂OCH₂CH₂-group; and R⁶ = C1-3 alkyl; and pharmaceutically-acceptable salts thereof are effective phospholipase A₂ (PLA₂) inhibitors.

  式 I 的化合物： 其中 C₂ 与 C3 之间和/或 C₄ 与 C₅ 之间的键为不饱和键； X = COOH、H、F、Cl、Br、I、COOR''、CONH₂、COR'''、CHO、CH₂OH、CH₂OR'''、OH、OR'''、CF₃、C1-6 烷基、C1-6 烯基、C1-6 卤代烷基、NO₂、P(O)(OH)₂、SO₂H 或 SO₃H； R = 取代或未取代的烷基、芳基、芳烷基、烯基或芳烷烯基，但这些基团都必须具有 6 个或更多的碳原子（最好是 6 至 30 个），且 R 不能是 R' = H 或 C1-6 烷基； R''=H、C1-6 烷基、C(R³)₂OC(O)R⁴、CH₂CH₂NR⁵R⁶、CH₂CH₂CH₂NR⁵R⁶、CH₂C(O)N(R⁶)₂ 或其他可产生生理性水解酯的基团； R''' = C1-6 烷基； R³ = H、CH₃、C₂H₅、CH₃CH₂CH₂（R³'s 相同或不同）； R⁴ = C6-12 芳基，C1-7 直链、支链或环状烷基，或 C1-7 直链、支链或环状烷氧基； R⁵ = R⁶，或当与 R⁶ 连接时，为 C₃-C₆ 环烷基或-CH₂CH₂OCH₂CH₂基团；以及 R⁶ = C1-3 烷基； 及其药学上可接受的盐是有效的磷脂酶 A₂（PLA₂）抑制剂。