1-[[4-(三氟甲氧基)苯基]磺酰基]哌嗪 | 756859-05-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-[[4-(三氟甲氧基)苯基]磺酰基]哌嗪
• 英文名称: 1-((4-(trifluoromethoxy)phenyl)sulfonyl)piperazine
• 英文别名: 1-[4-(Trifluoromethoxy)benzenesulfonyl]piperazine；1-[4-(trifluoromethoxy)phenyl]sulfonylpiperazine
• CAS: 756859-05-9
• 化学式: C₁₁H₁₃F₃N₂O₃S
• mdl: MFCD06341994
• 分子量: 310.297
• InChiKey: YNZSAWALMDCRMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.454
• 拓扑面积：
  67
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-[[4-(三氟甲氧基)苯基]磺酰基]哌嗪 在 氢溴酸 、 palladium diacetate 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 甲苯 为溶剂， 反应 18.5h， 生成
  参考文献：
  名称：

  Synthesis and Structure–Activity Relationships for Extended Side Chain Analogues of the Antitubercular Drug (6S)-2-Nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824)

  摘要：

  Novel extended side chain nitroimidazooxazine analogues featuring diverse linker groups between two aryl rings were studied as a potential strategy to improve solubility and oral activity against chronic infection by Mycobacterium tuberculosis. Both lipophilic and highly polar functionalities (e.g., carboxamide, alkylamine, piperazine, piperidine, but not sulfonamide) were well tolerated in vitro, and the hydrophilic linkers provided some solubility improvements, particularly in combination with pyridine rings. Most of the 18 compounds further assessed showed high microsomal stabilities, although in the acute infection mouse model, just one stilbene (6-fold) and two pyridine-containing acetylene derivatives (5-fold and >933-fold) gave in vivo efficacies notably superior to the clinical stage compound pretomanid (PA-824). The most efficacious analogue also displayed outstanding in vivo activity in the stringent chronic model (up to 24-fold better than the drug delamanid and 4-fold greater than our previous best phenylpyridine candidate), with favorable pharmacokinetics, including good oral bioavailability in the rat.

  DOI：

  10.1021/jm501608q
• 作为产物：
  描述：

  4-(三氟甲氧基)苯磺酰氯 在 盐酸 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 1-[[4-(三氟甲氧基)苯基]磺酰基]哌嗪
  参考文献：
  名称：

  [EN] PIPERAZINE DERIVATIVES FOR BLOCKING Cav2.2 CALCIUM CHANNELS
  [FR] DÉRIVÉS DE PIPÉRAZINE POUR BLOQUER DES CANAUX CALCIQUES CAV2.2

  摘要：

  本发明涉及新型哌嗪化合物；含有这些化合物的药物组合物；以及利用这些化合物在治疗中对治疗阻断Cav2.2钙通道有益的疾病和对治疗阻断Cav2.2和Cav3.2钙通道有益的疾病，例如治疗疼痛。

  公开号：

  WO2011086377A1

文献信息

• Sulfonylpiperazines based on a flavone as antioxidant and cytotoxic agents
  作者：Rahul V. Patel、Bhupendra M. Mistry、Riyaz Syed、Nikhil M. Parekh、Han‐Seung Shin

  DOI：10.1002/ardp.201900051

  日期：2019.9

  Chrysin‐based sulfonylpiperazines 7a‐k were synthesized and investigated for their in vitro free radical scavenging potential as well as cytotoxic efficacies against selected cancer cell lines. Cytotoxicity of the new compounds toward noncancer cells was confirmed using the SRB assay against Madin–Darby Canine Kidney cells. Reaction of piperazine with different substituted benzenesulfonyl chlorides

  合成了基于白杨素的磺酰基哌嗪 7a-k，并研究了它们的体外自由基清除能力以及对选定癌细胞系的细胞毒性作用。使用针对 Madin-Darby 犬肾细胞的 SRB 测定证实了新化合物对非癌细胞的细胞毒性。哌嗪与不同取代苯磺酰氯在三乙胺提供的磺酰哌嗪 (3a-k) 中反应，然后与 7-(4-溴丁氧基)-5-羟基-2-苯基-4H-色胺-4-酮 (6 ) 制备白杨素与 1,4-二溴丁烷反应得到最终衍生物 7a-k。结果表明，白杨素-磺酰基哌嗪比以前研究的白杨素-哌嗪前体具有更好的抗氧化和抗癌功效。例如，化合物 7h、7j 和 7k 与 4-OCF3、4-OCH3、和 2,4-diOCH3 基团对 2,2-diphenyl-1-picrylhydrazyl (DPPH) 和 2,2'-azino-bis-3-ethylbenzothiazoline-6-sulfonic acid (ABTS) 自由基
• [EN] DERIVATIVES OF HYDROXAMIC ACID AS METALLOPROTEINASE INHIBITORS<br/>[FR] DERIVES D'ACIDE HYDROXAMIQUE UTILISES COMME INHIBITEURS DE METALLOPROTEINASES
  申请人：VERNALIS OXFORD LTD

  公开号：WO2005019194A1

  公开（公告）日：2005-03-03

  Compounds of formula (I) are inhibitors of matrix metalloproteinases, and are of use in the treatment of, for example fibrotic disease, multiple sclerosis, emphysemia, bronchitis and asthma: formula (I) wherein Ar represents an optionally substituted aryl, heteroaryl, C3-C8 cycloalkyl or heterocycloakyl group; R represents hydrogen or C1-C6 alkyl, or C3-C6 cycloalkyl; Alk represents a divalent C1-C5 alkylene or C2-C5 alkenylene radical; and R1 and R2 taken together with the nitrogen atom to which they are attached form a first heterocycloalkyl ring which is optionally fused to a second C3-C8 cycloalkyl or heterocycloalkyl ring, the said first and second rings being optionally substituted by at least one group of formula (II): formula (II) wherein m, p and n are independently 0 or 1; Z represents, hydrogen, or an optionally substituted carbocyclic or heterocyclic ring of from 5 to 7 ring atoms which is optionally fused to another optionally substituted carbocyclic or heterocyclic ring of from 5 to 7 ring atoms; Alk1 and Alk2 independently represent optionally substituted divalent C1-C3 alkylene radicals; X represents -0-, -S-, -S(O)-, -S(O2)-, -C(=O)-, -NH-, -NR3-, -S(O2)NH-, -S(O2)NR3-, -NHS(O2)-, or -NR3S(O2)-, where R3 is C1-C3 alkyl.

  式(I)的化合物是基质金属蛋白酶的抑制剂，并可用于治疗纤维化疾病、多发性硬化症、肺气肿、支气管炎和哮喘等疾病：式(I)中Ar代表可选择地取代的芳基、杂环芳基、C3-C8环烷基或杂环烷基基团；R代表氢或C1-C6烷基，或C3-C6环烷基；Alk代表二价的C1-C5烷基或C2-C5烯基基团；R1和R2与它们连接的氮原子一起形成第一杂环烷基环，该环可选择地与第二个C3-C8环烷基或杂环烷基环融合，所述的第一和第二环可选择地被至少一个式(II)的基团取代：式(II)中m、p和n独立地为0或1；Z代表氢，或由5至7个环原子组成的可选择地取代的碳环或杂环环，该环可选择地与另一个由5至7个环原子组成的可选择地取代的碳环或杂环环融合；Alk1和Alk2独立地代表可选择地取代的二价的C1-C3烷基基团；X代表-0-、-S-、-S(O)-、-S(O2)-、-C(=O)-、-NH-、-NR3-、-S(O2)NH-、-S(O2)NR3-、-NHS(O2)-或-NR3S(O2)-，其中R3为C1-C3烷基。
• Novel Derivatives
  申请人：Heer Jag Paul

  公开号：US20100016330A1

  公开（公告）日：2010-01-21

  The present invention relates to novel piperazine derivatives; to processes for their preparation; to pharmaceutical compositions containing the derivatives; and to the use of the derivatives in therapy to treat diseases for which blocking the Ca v 2.2 calcium channels is beneficial.

  本发明涉及新颖的哌嗪衍生物；其制备方法；含有这些衍生物的药物组合物；以及利用这些衍生物在治疗中治疗阻断Ca v 2.2钙通道有益的疾病。
• PIPERAZINE DERIVATIVES FOR BLOCKING Cav2.2 CALCIUM CHANNELS
  申请人：Heer Jag Paul

  公开号：US20130072499A1

  公开（公告）日：2013-03-21

  The present invention relates to novel piperazine compounds; to pharmaceutical compositions containing the compounds; and to the use of the compounds in therapy to treat diseases for which blocking the Ca v 2.2 calcium channels is beneficial and to treat diseases for which blocking the Ca v 2.2 and Ca v 3.2 calcium channels is beneficial, e.g. to treat pain.

  本发明涉及新型哌嗪化合物；含有这些化合物的药物组合物；以及利用这些化合物在治疗中治疗阻断Ca v 2.2钙通道有益的疾病，以及治疗阻断Ca v 2.2和Ca v 3.2钙通道有益的疾病，例如治疗疼痛。
• Synthesis of Novel Benzamide- piperazine-sulfonamide Hybrids as Potential Anticancer Agents
  作者：B. Ramalingeswara Rao、Mohana Rao Katiki、Dileep Kommula、SaiShyam Narayanan、Ruby John Anto、M. S. R. Murty

  DOI：10.5562/cca3535

  日期：——

  The synthesis of a series of substituted hippuric acid (2-benzamidoacetic acid) derivatives containing arylsulfonylpiperazine nucleus (3a–j, 4a–j) is described. The compounds were synthesized by coupling hippuric/4-fluorohippuric acid with various arylsulfonylpiperazines using N-(3-dimethylaminopropyl)-N-ethylcarbodiimide (EDCI). The structures of all the new compounds were confirmed by IR, NMR and MS spectral data. All the synthesized compounds have been evaluated for their in vitro cytotoxicity towards five human cancer cell lines of different origins viz. HeLa (Cervical), A549 (Lung), A375 (Skin), MD-AMB-231(Breast) and T98G (brain) and their IC50 values were determined. Among the compounds tested, 3b, 3d, 3g, 4c and 4e displayed significant cytotoxic activity (IC50 = 24.2–38.2 µM). T98G was the most sensitive cell line towards the compounds studied followed by HeLa, A375, A549 and MD-AMB-231.

  一系列取代的苯甲酰基氨基乙酸（2-苯甲酰胺基乙酸）衍生物合成了含有芳基磺酰基哌嗪核（3a-j，4a-j）。这些化合物是通过使用N-(3-二甲基氨基丙基)-N-乙基碳二亚胺（EDCI）将苯甲酰基/4-氟苯甲酰基酸与各种芳基磺酰基哌嗪偶联合成的。所有新化合物的结构均通过红外光谱、核磁共振和质谱数据得到确认。所有合成的化合物均已评估其对五种不同来源的人类癌细胞系（即宫颈癌HeLa，肺癌A549，皮肤癌A375，乳腺癌MD-AMB-231和脑癌T98G）的体外细胞毒性，并确定了它们的IC50值。在测试的化合物中，3b、3d、3g、4c和4e显示出显著的细胞毒性活性（IC50 = 24.2-38.2 µM）。T98G是对所研究的化合物最敏感的细胞系，其次是HeLa、A375、A549和MD-AMB-231。