6-氟-2,3,4,9-四氢-1H-吡啶并[3,4-b]吲哚 | 17952-80-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 6-氟-2,3,4,9-四氢-1H-吡啶并[3,4-b]吲哚
• 英文名称: 6-fluoro-2,3,4,9-tetrahydro-1H-pyridino[3,4-b]indole
• 英文别名: 6-fluoro-2,3,4,9-tetrahydro-1H-β-carboline；6-fluoro-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole；6-fluoro-2,3,4,9-tetrahydro-1H-β-carboline；6-Fluor-1,2,3,4-tetrahydro-norharmalin；6-Fluor-tetrahydro-β-carbolin
• CAS: 17952-80-6
• 化学式: C₁₁H₁₁FN₂
• mdl: MFCD07364735
• 分子量: 190.22
• InChiKey: ZRBOYHOKTLJAAM-UHFFFAOYSA-N

物化性质

• 沸点：
  355.1±37.0 °C(Predicted)
• 密度：
  1.277±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  27.8
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-氟-2,3,4,9-四氢-1H-吡啶并[3,4-b]吲哚 以73.9%的产率得到6-Fluro-2,3,4,9-Tetrahydro-2-[2-(2-Pyridinyl)ethyl]1H-pyrido[3,4-b]indole, dihydrochloride
  参考文献：
  名称：

  2,3,4,9-tetrahydro-2-heteroarylalkyl-1H-pyrido(3,4-B)indoles having

  摘要：

  这项发明涉及公式为的四氢吡啶吲哚：其中Q代表其中R.sub.3为氢，C.sub.1-4烷基，C.sub.1-4烷氧基或--COO(C.sub.1-2)烷基，n为1到7的整数；R.sub.1为氢，卤素，羟基或C.sub.1-3烷基；R.sub.2为氢，C.sub.1-4烷基或--(CH.sub.2).sub.m --A，其中A为--N(CH.sub.3).sub.2，--N(C.sub.2 H.sub.5).sub.2，其中Ar为2-嘧啶基，2-吡啶基，苯基或被甲基，乙基，甲氧基，乙氧基或三氟甲基基取代的苯基；m为1-4的整数，或其生理上可接受的盐，但当n为1时，Q可能不是喹啉基。这些化合物具有降压作用。所述的四种化合物还具有抗精神病作用。还披露了公式为XX的化合物，其中公式I的Q被Q.sub.1取代，其中Q.sub.1为2-或3-吡啶基，公式I的R.sub.2限制为氢。公式XX的化合物具有抗精神病作用。

  公开号：

  US04719211A1
• 作为产物：
  描述：

  6-fluoro-2,3,4,9-tetrahydro-β-carbolin-1-one 在 lithium aluminium tetrahydride 作用下， 以 1,4-二氧六环 为溶剂， 生成 6-氟-2,3,4,9-四氢-1H-吡啶并[3,4-b]吲哚
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Novel Tetrahydro-β-carboline Derivatives as Antitumor Growth and Metastasis Agents through Inhibiting the Transforming Growth Factor-β Signaling Pathway

  摘要：

  The transforming growth factor beta (TGF beta) signaling cascade is considered as one of the pivotal oncogenic pathways in most advanced cancers. Inhibition of the TGF beta signaling pathway by specific antagonists, neutralizing antibodies, or small molecules is considered as an effective strategy for the treatment of tumor growth and metastasis. Here we demonstrated the identification of a series of tetrahydro-beta-carboline derivatives from virtual screening which potentially inhibit the TGF beta signaling pathway. Optimization of the initial hit compound 2-benzoyl-1,3,4,9-tetrahydro-beta-carboline (8a) through substitution at different positions to define the structure-activity relationship resulted in the discovery of potent inhibitors of the TGF beta signaling pathway. Among them, compound 8d, one of the tested compounds, not only showed potent inhibition of lung cancer cell proliferation and migration in vitro but also strongly suppressed growth of lung cancer and breast cancer in vivo.

  DOI：

  10.1021/jm401117t

文献信息

• [EN] TETRAHYDROBENZOFURO[2,3-C]PYRIDINE AND BETA-CARBOLINE COMPOUNDS FOR THE TREATMENT, ALLEVIATION OR PREVENTION OF DISORDERS ASSOCIATED WITH TAU AGGREGATES<br/>[FR] COMPOSÉS DE TÉTRAHYDROBENZOFURO[2,3-C]PYRIDINE ET DE BÊTA-CARBOLINE POUR LE TRAITEMENT, LE SOULAGEMENT OU LA PRÉVENTION DE TROUBLES ASSOCIÉS À DES AGRÉGATS DE PROTÉINE TAU
  申请人：AC IMMUNE SA

  公开号：WO2019233883A1

  公开（公告）日：2019-12-12

  The present invention relates to novel compounds of formula (I) that can be employed in the treatment, alleviation or prevention of a group of disorders and abnormalities associated with Tau (Tubulin associated unit) protein aggregates including, but not limited to, Neurofibrillary Tangles (NFTs), such as Alzheimer's disease (AD).

  本发明涉及一种可以用于治疗、缓解或预防与Tau（微管相关单元）蛋白聚集相关的一组疾病和异常的新化合物（I）的公式。这些疾病和异常包括但不限于神经原纤维缠结（NFTs），如阿尔茨海默病（AD）。
• Inhibitors of histone deacetylase
  申请人：Anandan K. Sampath

  公开号：US20060199829A1

  公开（公告）日：2006-09-07

  Disclosed are compounds of formula I that inhibit histone deacetylase (HDAC) enzymatic activity, pharmaceutical compositions comprising such compounds, as well as methods to treat conditions, particularly proliferative conditions, mediated at least in part by HDAC, wherein A, W, W 1 , W 2 , Ar 2 , and G are described herein.

  本发明涉及公式I的化合物，其抑制组蛋白去乙酰化酶（HDAC）酶活性，包括这样的化合物的制药组合物，以及用于治疗至少部分由HDAC介导的疾病，特别是增殖性疾病的方法，其中A，W，W1，W2，Ar2和G如本文所述。
• Nucleoside derivatives for treating hepatitis C virus infection
  申请人：——

  公开号：US20040063658A1

  公开（公告）日：2004-04-01

  Disclosed are compounds, compositions and methods for treating hepatitis C virus infections.

  本发明涉及用于治疗丙型肝炎病毒感染的化合物、组合物和方法。
• Indazole compound and pharmaceutical use thereof
  申请人：Takemiya Akihiro

  公开号：US20070173537A1

  公开（公告）日：2007-07-26

  The present invention can provide a cancer treatment drug containing, as an active ingredient, a substance selected from the group consisting of an indazole compound of the following formula (I), a pharmaceutically acceptable salt, a hydrate, a water adduct and a solvate:

  本发明可以提供一种癌症治疗药物，其包含以下公式（I）中的吲唑化合物、药用可接受盐、水合物、水加合物和溶剂化物等物质中所选的一种作为活性成分：
• Serotonergic modulators
  申请人：LILLY INDUSTRIES LIMITED

  公开号：EP0705832A1

  公开（公告）日：1996-04-10

  A pharmaceutical compound of the formula in which R¹ and R⁷ are each halo, trifluoromethyl, C₁₋₆ alkyl, C₁₋₆ alkoxy, optionally substituted phenyl, optionally substituted naphthyl or optionally substituted heteroaryl, R and R³ are each hydrogen or C₁₋₆ alkyl, R⁴ and R⁵ are each hydrogen, halo, trifluoromethyl, C₁₋₆ alkyl, C₁₋₆ alkoxy, optionally substituted phenyl, optionally substituted naphthyl or optionally substituted heteroaryl, R⁶ is hydrogen, C₁₋₆ alkyl, optionally substituted phenyl, optionally substituted naphthyl, optionally substituted heteroaryl, optionally substituted phenyl-C₁₋₆ alkyl or -CO₂R⁸ where R⁸ is an ester group, m and p are each 0, 1, 2, 3 or 4, n is 1, 2, 3 or 4, Z is where R⁹ and R¹⁰ are each hydrogen, C₁₋₆ alkyl or optionally substituted phenyl-C₁₋₆ alkyl, X is oxygen or sulphur, and Y is where R¹¹ and R¹ are each hydrogen, C₁₋₆ alkyl, trifluoromethyl, optionally substituted phenyl, optionally substituted naphthyl or optionally substituted heteroaryl; and salts and solvates thereof. The compounds of the invention are indicated for use in the treatment of diseases of the central nervous system. They are active in tests that indicate serotonergic modulation.

  一种药物化合物，其式如下 其中 R¹ 和 R⁷ 分别为卤素、三氟甲基、C₁₋₆ 烷基、C₁₋₆ 烷氧基、任选取代的苯基、任选取代的萘基或任选取代的杂芳基、R 和 R³ 分别是氢或 C₁₋₆ 烷基，R⁴ 和 R⁵ 分别是氢、卤代、三氟甲基、C₁₋₆ 烷基、C₁₋₆ 烷氧基、任选取代的苯基、R⁶是氢、C₁₋₆烷基、任选取代的苯基、任选取代的萘基或任选取代的杂芳基、任选取代的杂芳基、任选取代的苯基-C₁₋₆烷基或-CO₂R⁸，其中 R⁸ 是酯基，m 和 p 分别是 0、1、2、3 或 4，n 是 1、2、3 或 4。 其中 R⁹ 和 R¹⁰ 各为氢、C₁₋₆ 烷基或任选取代的苯基-C₁₋₆ 烷基，X 为氧或硫，Y 为 其中 R¹¹ 和 R¹ 各为氢、C₁₋₆ 烷基、三氟甲基、任选取代的苯基、任选取代的萘基或任选取代的杂芳基； 及其盐类和溶剂。 本发明的化合物可用于治疗中枢神经系统疾病。它们在显示血清素能调节的试验中具有活性。