4-(三氟甲基)-1H-吲唑 | 1000339-98-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 中文名称: 4-(三氟甲基)-1H-吲唑
• 英文名称: 4-(trifluoromethyl)-1H-indazole
• CAS: 1000339-98-9
• 化学式: C₈H₅F₃N₂
• mdl: MFCD09263211
• 分子量: 186.136
• InChiKey: KCWIWQGNCLKDJZ-UHFFFAOYSA-N

物化性质

• 沸点：
  268.5±35.0 °C(Predicted)
• 密度：
  1.447±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  4-(三氟甲基)-1H-吲唑 在 盐酸 、 碳酸氢钠 、 magnesium sulfate 、 caesium carbonate 、 tin(ll) chloride 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-[4-(Trifluoromethyl)indazol-1-yl]aniline
  参考文献：
  名称：

  Synthesis of indazole based diarylurea derivatives and their antiproliferative activity against tumor cell lines

  摘要：

  New series of indazole based diarylureas were synthesized and their anticancer activity against cancer cells H460, A549, OS-RC-2, HT-29, Lovo, HepG2, Bel-7402, SGC-7901 and MDA-MB-231 were examined. These derivatives of diarylureas, except azaindazole based diarylureas 5f, 51 and 5m, showed superior or similar activity against most of these selected cancer cell lines to the reference compound sorafenib. The effect of substituents on the indazole ring was also investigated. Derivatives with trifluoromenthy or halogen substituents on the indazole ring showed higher activity against the selected cancer cell lines than sorafenib. The acute toxicity assay showed that compounds 5a, 5b and 5i possessed lower toxicity than sorafenib. Compound 5i with 4-(trifluoromenthy)-1H-indazole and 4-(trifluoromenthy) benzene moieties exhibited the most potent anticancer activity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.02.034

文献信息

• [EN] RORGAMMAT INHIBITORS<br/>[FR] INHIBITEURS DE RORGAMMAT
  申请人：MERCK SHARP & DOHME

  公开号：WO2012106995A1

  公开（公告）日：2012-08-16

  The present invention relates to compounds according to Formula (I) or a pharmaceutically acceptable salt or solvate thereof. Such compounds can be used in the treatment of RORgammaT-mediated diseases or condition.

  本发明涉及按照式(I)的化合物或其药用可接受的盐或溶剂。这些化合物可用于治疗RORgammaT介导的疾病或症状。
• New CRTh2 antagonists.
  申请人：Almirall, S.A.

  公开号：EP2548863A1

  公开（公告）日：2013-01-23

  The present invention relates to compounds of formula (I), to the process for preparing such compounds and to their use in the treatment of a pathological condition or disease susceptible to amelioration by CRTh2 antagonist activity.

  这项发明涉及到式(I)化合物，制备这种化合物的方法以及它们在治疗病理状况或疾病中的应用，这些病理状况或疾病对CRTh2拮抗活性有改善作用。
• 2-[3-(ALKYLSULFONYL)-2H-INDAZOL-2-YL]-3H-IMIDAZO[4,5-B]PYRIDINE DERIVATIVES AND SIMILAR COMPOUNDS AS PESTICIDES
  申请人：BAYER CROPSCIENCE AKTIENGESELLSCHAFT

  公开号：US20190274306A1

  公开（公告）日：2019-09-12

  The invention relates to compounds of the formula (Ia) or (Ib), in which Aa, Ab, Ac, Ad, R 1 , R 10 R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , Q, R4, R 5 , R 6 and have the meanings indicated in the claims, and to agrochemical formulations containing the compounds according to formula (Ia) or (Ib) for use as acaricides and/or insecticides for combating animal pests, primarily arthropods and in particular insects and arachnids. 2-[3-(alkylsulfonyl)-2H-indazol-2-yl]-3H-imidazo[4,5-b]pyridine derivatives and similar compounds are particularly preferable.

  该发明涉及化合物的公式(Ia)或(Ib)，其中Aa、Ab、Ac、Ad、R1、R10R11、R12、R13、R14、R15、R16、R17、Q、R4、R5、R6具有索赔中指示的含义，并且涉及包含根据公式(Ia)或(Ib)的化合物的农药配方，用作螨虫和/或昆虫的杀虫剂，主要用于对抗动物害虫，特别是节肢动物，尤其是昆虫和蜘蛛。2-[3-(烷基磺酰基)-2H-吲哚-2-基]-3H-咪唑[4,5-b]吡啶衍生物和类似化合物特别可取。
• Discovery of indazole aldosterone synthase (CYP11B2) inhibitors as potential treatments for hypertension
  作者：Scott B. Hoyt、Jerry Taylor、Clare London、Amjad Ali、Feroze Ujjainwalla、Jim Tata、Mary Struthers、Doris Cully、Tom Wisniewski、Ning Ren、Charlene Bopp、Andrea Sok、Andreas Verras、Daniel McMasters、Qing Chen、Elaine Tung、Wei Tang、Gino Salituro、Joe Clemas、Gaochao Zhou、Douglas MacNeil、Ruth Duffy、Yusheng Xiong

  DOI：10.1016/j.bmcl.2017.04.021

  日期：2017.6

  We report the discovery and hit-to-lead optimization of a structurally novel indazole series of CYP11B2 inhibitors. Benchmark compound 34 from this series displays potent inhibition of CYP11B2, high selectivity versus related steroidal and hepatic CYP targets, and lead-like physical and pharmacokinetic properties. On the basis of these and other data, the indazole series was progressed to lead optimization

  我们报告了一种结构新颖的吲唑系列CYP11B2抑制剂的发现和领先优势。该系列的基准化合物34显示出对CYP11B2的有效抑制作用，相对于相关的甾体和肝CYP靶标具有很高的选择性，以及类似铅的物理和药代动力学特性。根据这些数据和其他数据，将吲唑系列进行了优化，以进一步精制。
• Rational drug design of indazole-based diarylurea derivatives as anticancer agents
  作者：Yan-yan Chu、He-juan Cheng、Zhen-hua Tian、Jian-chun Zhao、Gang Li、Yang-yang Chu、Chang-jun Sun、Wen-bao Li

  DOI：10.1111/cbdd.12984

  日期：2017.10

  series of novel indazole-based diarylurea derivatives targeting c-kit were designed by structure-based drug design. The derivatives were prepared, and their antiproliferative activities were evaluated against human colon cancer HCT-116 cell line and hepatocellular carcinoma PLC/PRF/5 cell line. The antiproliferative activities demonstrated that six of nine compounds exhibited comparable activities with

  通过基于结构的药物设计，设计了一系列靶向c-kit的新型基于吲唑的二芳基脲衍生物。制备衍生物，并评估其对人结肠癌HCT-116细胞系和肝细胞癌PLC / PRF / 5细胞系的抗增殖活性。抗增殖活性表明，九种化合物中的六种显示出与索拉非尼相当的抗HCT-116活性。结构-活性关系（SAR）分析表明，吲唑环部分可耐受不同种类的取代基，中央吡啶环的N位置在抗增殖活性中起关键作用。使用分子对接方法进一步探索了SAR和相互作用机理。化合物1i与N- （2-（吡咯烷-1-基）乙基） -甲酰胺且具改善的溶解度，596.1毫微克/毫升，最好的活动，IC 50为1.0μ米针对HCT-116，和3.48μ米针对PLC / PRF / 5。它是有前途的抗癌药物。