1,1,1-trifluoro-4-hydroxy-4-phenanthren-2-yl-but-3-en-2-one | 882854-63-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 1,1,1-trifluoro-4-hydroxy-4-phenanthren-2-yl-but-3-en-2-one
• 英文别名: 1,1,1-Trifluoro-4-hydroxy-4-phenanthren-2-yl-but-3-en-2-one；1,1,1-trifluoro-4-hydroxy-4-phenanthren-2-ylbut-3-en-2-one
• CAS: 882854-63-9
• 化学式: C₁₈H₁₁F₃O₂
• 分子量: 316.279
• InChiKey: UTGUBKPWCMIXQL-UHFFFAOYSA-N

物化性质

• 沸点：
  441.4±45.0 °C(Predicted)
• 密度：
  1.377±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,1,1-trifluoro-4-hydroxy-4-phenanthren-2-yl-but-3-en-2-one 、 4-磺酰胺基苯肼盐酸盐 以 乙醇 为溶剂， 反应 12.0h， 以80%的产率得到OSU-02067
  参考文献：
  名称：

  ANTI-INFECTIVE AGENTS AGAINST INTRACELLULAR PATHOGENS

  摘要：

  一种新的磷脂酰肌醇依赖激酶-1（PDK-1）抑制剂的化学式I：其中X为—CF3，Ar从中选择，R从中选择，其中R′为L-赖氨酸，D-赖氨酸，β-丙氨酸，L-亮氨酸，L-异亮氨酸，苯丙氨酸，SO2CH2CH2NH2，SO2NH2，天冬氨酸，谷氨酸或甘氨酸，R″为甲基，乙基，烯丙基，CH2CH2OH，CH2CN，CH2CH2CN，CH2CONH2。

  公开号：

  US20090111799A1
• 作为产物：
  描述：

  三氟乙酸乙酯 、 2-乙酰基菲 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.67h， 以90%的产率得到1,1,1-trifluoro-4-hydroxy-4-phenanthren-2-yl-but-3-en-2-one
  参考文献：
  名称：

  ANTI-INFECTIVE AGENTS AGAINST INTRACELLULAR PATHOGENS

  摘要：

  一种新的磷脂酰肌醇依赖激酶-1（PDK-1）抑制剂的化学式I：其中X为—CF3，Ar从中选择，R从中选择，其中R′为L-赖氨酸，D-赖氨酸，β-丙氨酸，L-亮氨酸，L-异亮氨酸，苯丙氨酸，SO2CH2CH2NH2，SO2NH2，天冬氨酸，谷氨酸或甘氨酸，R″为甲基，乙基，烯丙基，CH2CH2OH，CH2CN，CH2CH2CN，CH2CONH2。

  公开号：

  US20090111799A1

文献信息

• PDK-1/Akt signaling inhibitors
  申请人：Chen Ching-Shih

  公开号：US20060079566A1

  公开（公告）日：2006-04-13

  A new class of phosphoinositide-dependent kinase-1 (PDK-1) inhibitors of formula I: wherein X is selected from the group consisting of alkyl and haloalkyl; Ar is an aryl radical selected from the group consisting of phenyl, biphenyl, naphthyl, anthryl, phenanthryl, and fluorenyl; and wherein Ar is optionally substituted with one or more radicals selected from the group consisting of halo, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, azido, C 1 -C 4 azidoalkyl, aryl, akylaryl, haloaryl, haloalkylaryl, and combinations thereof; and R is selected from the group consisting of nitrile, acetonitrile, ethylnitrile, propylnitrile, carboxamide, amidine, tetrazole, oxime, hydrazone, acetamidine, aminoacetamide, guanidine, and urea. Also provided are methods of using the compounds for the treatment and prevention of cancer in humans.

  一种新型的磷脂酰肌醇依赖性激酶-1（PDK-1）抑制剂，其化学式为I：其中X选自烷基和卤代烷基；Ar为苯基、联苯基、萘基、蒽基、菲基和芴基中选择的芳基基团；其中Ar可选地被一个或多个选自卤素、C1-C4烷基、C1-C4卤代烷基、偶氮、C1-C4偶氮烷基、芳基、烷基芳基、卤代芳基、卤代烷基芳基和其组合的基团取代；R选自腈、乙腈、丙腈、羧酰胺、胍、四唑、肟、腙、乙酰胍、氨基乙酰胺、胍、尿素中选择的基团。此外，还提供了使用该化合物治疗和预防人类癌症的方法。
• PDK-1/AKT SIGNALING INHIBITORS
  申请人：Chen Ching-Shih

  公开号：US20080269309A1

  公开（公告）日：2008-10-30

  Use of a new class of phosphoinositide-dependent kinase-1 (PDK-1) inhibitors of formula I for inducing apoptosis in unwanted rapidly proliferating cells, for treating, inhibiting, or delaying the onset of cancer, and for preventing restenosis in a subject that has undergone an angioplasty or stent: wherein X is selected from the group consisting of alkyl and haloalkyl; Ar is an aryl radical selected from the group consisting of phenyl, biphenyl, naphthyl, anthryl, phenanthryl, and fluorenyl; and wherein Ar is optionally substituted with one or more radicals selected from the group consisting of halo, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, azido, C 1 -C 4 azidoalkyl, aryl, akylaryl, haloaryl, haloalkylaryl, and combinations thereof; and R is selected from the group consisting of nitrile, acetonitrile, ethylnitrile, propylnitrile, carboxamide, amidine, tetrazole, oxime, hydrazone, acetamidine, aminoacetamide, guanidine, and urea.

  使用一种新的磷脂酰肌醇依赖性激酶-1（PDK-1）抑制剂（I式）用于诱导不需要的快速增殖细胞凋亡，用于治疗、抑制或延迟癌症发生，并用于预防经过血管成形术或支架的患者再狭窄：其中X选自烷基和卤代烷基的群体；Ar是选自苯基、联苯基、萘基、蒽基、菲基和芴基的芳基基团；其中Ar可选地被一个或多个选自卤素、C1-C4烷基、C1-C4卤代烷基、叠氮基、C1-C4叠氮基烷基、芳基、烷基芳基、卤代芳基、卤代烷基芳基和其组合的基团取代；R选自腈、乙腈、乙腈、丙腈、羧酰胺、胍、四唑、肟、酰肟、氨基乙酰胺、胍、尿素的群体。
• Anti-infective agents against intracellular pathogens
  申请人：The Ohio State University Research Foundation

  公开号：US08039502B2

  公开（公告）日：2011-10-18

  A new class of phosphoinositide-dependent kinase-1 (PDK-1) inhibitors of Formula I: wherein X wherein X is —CF3, Ar is selected from and R is selected from where R′ is L-Lys, D-Lys, β-Ala, L-Lue, L-Ile, Phe, SO2CH2CH2NH2, SO2NH2, Asn, Glu or Gyl, and R″ is methyl, ethyl, allyl, CH2CH2OH, CH2CN, CH2CH2CN, CH2CONH2,

  一种新型的磷脂酰肌醇依赖性激酶-1（PDK-1）抑制剂，其化学式为I：其中X为—CF3，Ar为以下之一：且R为以下之一：其中R′为L-Lys、D-Lys、β-Ala、L-Lue、L-Ile、Phe、SO2CH2CH2NH2、SO2NH2、Asn、Glu或Gyl，R″为甲基、乙基、烯丙基、CH2CH2OH、CH2CN、CH2CH2CN、CH2CONH2。
• PDK-1/AKT signaling inhibitors
  申请人：Chen Ching-Shih

  公开号：US08546441B2

  公开（公告）日：2013-10-01

  A new class of phosphoinositide-dependent kinase-1 (PDK-1) inhibitors of formula I: wherein X is selected from the group consisting of alkyl and haloalkyl; Ar is an aryl radical selected from the group consisting of phenyl, biphenyl, naphthyl, anthryl, phenanthryl, and fluorenyl; and wherein Ar is optionally substituted with one or more radicals selected from the group consisting of halo, C1-C4 alkyl, C1-C4 haloalkyl, azido, C1-C4 azidoalkyl, aryl, alkylaryl, haloaryl, haloalkylaryl, and combinations thereof; and R is selected from the group consisting of nitrile, acetonitrile, ethylnitrile, propylnitrile, carboxamide, amidine, tetrazole, oxime, hydrazone, acetamidine, aminoacetamide, guanidine, and urea. Also provided are methods of using the compounds for the treatment and prevention of cancer in humans.

  一种新型磷脂酰肌醇依赖性激酶-1（PDK-1）抑制剂的化学式I：其中X选自烷基和卤代烷基组成的群；Ar是从苯基、联苯基、萘基、蒽基、菲基和芴基组成的芳基基团中选出的一个；其中Ar可以选择性地用一个或多个从卤、C1-C4烷基、C1-C4卤代烷基、叠氮基、C1-C4叠氮基烷基、芳基、烷基芳基、卤代芳基、卤代烷基芳基及其组合的基团进行取代；R选自腈、乙腈、丙腈、羧酰胺、胍、四唑、肟、肼酰肼、氨基乙酰胺、胍、尿素组成的群。还提供了使用这些化合物治疗和预防人类癌症的方法。
• ANTI-INFECTIVE AGENTS AGAINST INTRACELLULAR PATHOGENS
  申请人：Chen Ching-Shih

  公开号：US20090111799A1

  公开（公告）日：2009-04-30

  A new class of phosphoinositide-dependent kinase-1 (PDK-1) inhibitors of Formula I: wherein X wherein X is —CF 3 , Ar is selected from and R is selected from where R′ is L-Lys, D-Lys, β-Ala, L-Lue, L-Ile, Phe, SO 2 CH 2 CH 2 NH 2 , SO 2 NH 2 , Asn, Glu or Gyl, and R″ is methyl, ethyl, allyl, CH 2 CH 2 OH, CH 2 CN, CH 2 CH 2 CN, CH 2 CONH 2 ,

  一种新的磷脂酰肌醇依赖激酶-1（PDK-1）抑制剂的化学式I：其中X为—CF3，Ar从中选择，R从中选择，其中R′为L-赖氨酸，D-赖氨酸，β-丙氨酸，L-亮氨酸，L-异亮氨酸，苯丙氨酸，SO2CH2CH2NH2，SO2NH2，天冬氨酸，谷氨酸或甘氨酸，R″为甲基，乙基，烯丙基，CH2CH2OH，CH2CN，CH2CH2CN，CH2CONH2。