1-(3-氟-4-硝基苯基)-4-异丙基哌嗪 | 1000051-20-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 中文名称: 1-(3-氟-4-硝基苯基)-4-异丙基哌嗪
• 英文名称: 1-(2-fluoro-4-nitrophenyl)-4-isopropylpiperazine
• 英文别名: 1-(2-fluoro-4-nitrophenyl)-4-propan-2-ylpiperazine
• CAS: 1000051-20-6
• 化学式: C₁₃H₁₈FN₃O₂
• 分子量: 267.303
• InChiKey: GLTABKREVWMODX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(3-氟-4-硝基苯基)-4-异丙基哌嗪 在 亚硝酸特丁酯 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 palladium 10% on activated carbon 、 氢气 、 potassium acetate 、 copper(ll) bromide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙腈 为溶剂， 反应 29.08h， 生成 1-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-4-isopropylpiperazine
  参考文献：
  名称：

  [EN] 1H-PYRROLO[3,2-C]PYRIDINE AND 1H-PYRROLO[2,3-C]PYRIDINE DERIVATIVES AS TLR9 INHIBITORS FOR THE TREATMENT OF FIBROSIS
  [FR] DÉRIVÉS DE 1H-PYRROLO[3,2-C]PYRIDINE ET DE 1H-PYRROLO[2,3-C]PYRIDINE EN TANT QU'INHIBITEURS DE TLR9 POUR LE TRAITEMENT DE LA FIBROSE

  摘要：

  本发明涉及式(I)或其盐的1H-吡咯并[3,2-c]吡啶和1H-吡咯并[2,3-c]吡啶衍生物。这些化合物是TLR9的抑制剂，可用于治疗、预防或减缓纤维化疾病，例如肝纤维化、肾脏纤维化、胆道纤维化或胰腺纤维化、非酒精性脂肪性肝病（NASH）、非酒精性脂肪肝病（NAFLD）、慢性肾脏病、糖尿病肾病、原发性硬化性胆管炎（PSC）或原发性胆汁性肝硬化（PBC）或特发性肺纤维化（IPF）。

  公开号：

  WO2022040267A1
• 作为产物：
  描述：

  1-异丙基哌嗪 、 3,4-二氟硝基苯 在 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 生成 1-(3-氟-4-硝基苯基)-4-异丙基哌嗪
  参考文献：
  名称：

  一种杂环化合物及其制备方法和应用

  摘要：

  本发明公开了一种杂环化合物及其制备方法和应用，所述杂环化合物具有以下结构： 其中，所述R1包括异丙基、乙基、环戊基、环丙基；R2包括甲基、氟；R3包括异丙基、氢、氟；R4包括异丙基、甲基、 本发明的杂环化合物对肿瘤细胞MDA‑MB‑231和MCF‑7都表现出很好的抑制活性。

  公开号：

  CN116003408A

文献信息

• N-(3,4-disubstituted phenyl) salicylamide derivatives
  申请人：TOKUYAMA Ryukou

  公开号：US20080227784A1

  公开（公告）日：2008-09-18

  A compound represented by the following formula (I) or a salt thereof: wherein R 1 , R 2 , R 3 and R 4 represent hydrogen atom, a halogen atom, cyano group, nitro group, a C 1-4 alkyl group, a halogenated C 1-4 alkyl group or a C 1-4 alkoxy group, R 5 represents a halogen atom, cyano group, a C 1-4 alkyl group, a halogenated C 1-4 alkyl group or a C 1-4 alkoxy group, R 6 represents a C 5-7 cycloalkyl group, a substituted C 5-7 cycloalkyl group, a 5 to 7-membered completely saturated heterocyclic group or a substituted 5 to 7-membered completely saturated heterocyclic group, X represents a single bond, oxygen atom, sulfur atom, NR 7 , —O—CH 2 — or —N(R 8 )—CH 2 —, R 7 represents hydrogen atom or a C 1-4 alkyl group, or R 7 may combine with a substituent of R 6 to represent a single bond, methylene group or ethylene group, R 8 represents hydrogen atom, a C 1-4 alkyl group or a C 7-12 aralkyl group, which is useful as an active ingredient of a medicament for prophylactic and/or therapeutic treatment of diseases caused by an activation of STAT6 and/or NF-κB.

  由以下式（I）表示的化合物或其盐：其中R1、R2、R3和R4代表氢原子、卤原子、氰基、硝基、C1-4烷基、卤代C1-4烷基或C1-4烷氧基，R5代表卤原子、氰基、C1-4烷基、卤代C1-4烷基或C1-4烷氧基，R6代表C5-7环烷基、取代的C5-7环烷基、5至7-成员完全饱和杂环基或取代的5至7-成员完全饱和杂环基，X代表单键、氧原子、硫原子、NR7、—O—CH2—或—N(R8)—CH2—，R7代表氢原子或C1-4烷基，或R7可以与R6的取代基结合以表示单键、亚甲基基团或乙烯基团，R8代表氢原子、C1-4烷基或C7-12芳基烷基，可用作药物的活性成分，用于预防和/或治疗由STAT6和/或NF-κB激活引起的疾病。
• Towards Optimization of Arylamides As Novel, Potent, and Brain-Penetrant Antiprion Lead Compounds
  作者：Zhe Li、Satish Rao、Joel R. Gever、Kartika Widjaja、Stanley B. Prusiner、B. Michael Silber

  DOI：10.1021/ml300454k

  日期：2013.7.11

  The prion diseases caused by PrPSc, in alternatively folded form of the cellular prion protein (PrPC), are rapidly progressive, fatal, and untreatable neurodegenerative disorders. We employed HTS ELISA assays to identify compounds that lower the level of PrPSc in prion-infected mouse neuroblastoma (ScN2a-cl3) cells and identified a series of arylamides. Structure-activity relationship (SAR) studies indicated that small amides with one aromatic or heteroaromatic ring on each side of the amide bond are of modest potency. Of note, benzamide (7), with an EC50 of 2200 nM, was one of only a few arylamide hits with a piperazine group on its aniline moiety. The basic piperazine nitrogen can be protonated at physiologic pH, improving solubility, and therefore, we wanted to exploit this feature in our search for a drug candidate. An SAR campaign resulted in several key analogues, including a set with biaryl groups introduced on the carbonyl side for improved potency. Several of these biaryl analogues have submicromolar potency, with the most potent analogue 17 having an EC50 = 22 nM. More importantly, 17 and several biarylamides (20, 24, 26, and 27) Were able to traverse the blood-brain barrier.(BBB) and displayed excellent drug levels in the brains of mice following oral dosing. These biarylamides, may represent good starting points for further lead optimization for the identification of potential drug candidates for the treatment of priori diseases.
• US7671058B2
  申请人：——

  公开号：US7671058B2

  公开（公告）日：2010-03-02
• [EN] 1H-PYRROLO[3,2-C]PYRIDINE AND 1H-PYRROLO[2,3-C]PYRIDINE DERIVATIVES AS TLR9 INHIBITORS FOR THE TREATMENT OF FIBROSIS<br/>[FR] DÉRIVÉS DE 1H-PYRROLO[3,2-C]PYRIDINE ET DE 1H-PYRROLO[2,3-C]PYRIDINE EN TANT QU'INHIBITEURS DE TLR9 POUR LE TRAITEMENT DE LA FIBROSE
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2022040267A1

  公开（公告）日：2022-02-24

  The present invention relates to 1H-pyrrolo[3,2-c]pyridine and 1H-pyrrolo[2,3-c]pyridine derivatives of formula (I) or a salt thereof. The present compounds are inhibitors of TLR9 and useful in treating preventing, or slowing fibrotic diseases, such as e.g. liver fibrosis, renal fibrosis, biliary fibrosis or pancreatic fibrosis, nonalcoholic steatohepatitis (NASH), non-alcoholic fatty liver disease (NAFLD), chronic kidney disease, diabetic kidney disease, primary sclerosing cholangitis (PSC) or primary biliary cirrhosis (PBC), or idiopathic pulmonary fibrosis (IPF).

  本发明涉及式(I)或其盐的1H-吡咯并[3,2-c]吡啶和1H-吡咯并[2,3-c]吡啶衍生物。这些化合物是TLR9的抑制剂，可用于治疗、预防或减缓纤维化疾病，例如肝纤维化、肾脏纤维化、胆道纤维化或胰腺纤维化、非酒精性脂肪性肝病（NASH）、非酒精性脂肪肝病（NAFLD）、慢性肾脏病、糖尿病肾病、原发性硬化性胆管炎（PSC）或原发性胆汁性肝硬化（PBC）或特发性肺纤维化（IPF）。
• Design and synthesis of 4th generation EGFR inhibitors against human triple (Del19/T790M/C797S) mutation
  作者：Jiyoung Jeon、Sun Young Jang、Eun Joo Kwak、Sun Hoe Lee、Joo-Yun Byun、Yu-Yon Kim、Young Gil Ahn、Pargat Singh、Kyeongwon Moon、In Su Kim

  DOI：10.1016/j.ejmech.2023.115840

  日期：2023.12