1-[(6-Hydrazinylpyridin-3-yl)sulfonyl]-4-methylpiperazine | 561012-68-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-[(6-Hydrazinylpyridin-3-yl)sulfonyl]-4-methylpiperazine
• 英文别名: [5-(4-methylpiperazin-1-yl)sulfonylpyridin-2-yl]hydrazine
• CAS: 561012-68-8
• 化学式: C₁₀H₁₇N₅O₂S
• mdl: MFCD04612888
• 分子量: 271.343
• InChiKey: LIVHBFWELMRSAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  99.9
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-[(6-Hydrazinylpyridin-3-yl)sulfonyl]-4-methylpiperazine 、 3,4-二羟基苯甲醛 以 乙醇 为溶剂， 生成
  参考文献：
  名称：

  Inhibition of cancer cell invasion by new ((3,4-dihydroxy benzylidene)hydrazinyl)pyridine-3-sulfonamide analogs

  摘要：

  Rab GTPases regulate various types of intracellular membrane trafficking in all eukaryotes. Since Rab27a and its multiple effectors are involved in exocytosis of lysosome-related organelles and play a major role in malignancy, compounds targeting Rab27a could be likely used to inhibit invasive growth and tumor metastasis. Thus, we designed and synthesized several compounds based on the previously reported Rab27a-targeting synthetic compounds identified by virtual screening, and investigated their anti-metastatic effects in MDA-MB231 and A375 cells. Among the synthesized compounds, (E)-N-(3-chlorophenyl)-6-(2-(3,4-dihydroxy benzylidene)hydrazinyl)pyridine-3-sulfonamide (3d) and (E)-N-benzyl-6-(2-(3,4-dihydroxy benzylidene)hydrazinyl)-N-methylpyridine-3-sulfonamide (3f) significantly inhibited the invasiveness of both tumor cell lines. Compounds 3d and 3f also decreased the levels of signature extracellular matrix marker proteins (fibronectin, collagen, and a-smooth muscle actin) and representative mesenchymal cell markers (N-cadherin and vimentin). Taken together, our results suggest that novel sulfonamide analogs have anti-metastatic activity in breast and melanoma cancer cell lines and may be used as therapeutic agents to treat malignant cancer. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.12.093
• 作为产物：
  描述：

  1-[(6-氯-3-吡啶基)磺酰基]-4-甲基-哌嗪 在 hydrazine hydrate 作用下， 以 乙醇 为溶剂， 生成 1-[(6-Hydrazinylpyridin-3-yl)sulfonyl]-4-methylpiperazine
  参考文献：
  名称：

  Inhibition of cancer cell invasion by new ((3,4-dihydroxy benzylidene)hydrazinyl)pyridine-3-sulfonamide analogs

  摘要：

  Rab GTPases regulate various types of intracellular membrane trafficking in all eukaryotes. Since Rab27a and its multiple effectors are involved in exocytosis of lysosome-related organelles and play a major role in malignancy, compounds targeting Rab27a could be likely used to inhibit invasive growth and tumor metastasis. Thus, we designed and synthesized several compounds based on the previously reported Rab27a-targeting synthetic compounds identified by virtual screening, and investigated their anti-metastatic effects in MDA-MB231 and A375 cells. Among the synthesized compounds, (E)-N-(3-chlorophenyl)-6-(2-(3,4-dihydroxy benzylidene)hydrazinyl)pyridine-3-sulfonamide (3d) and (E)-N-benzyl-6-(2-(3,4-dihydroxy benzylidene)hydrazinyl)-N-methylpyridine-3-sulfonamide (3f) significantly inhibited the invasiveness of both tumor cell lines. Compounds 3d and 3f also decreased the levels of signature extracellular matrix marker proteins (fibronectin, collagen, and a-smooth muscle actin) and representative mesenchymal cell markers (N-cadherin and vimentin). Taken together, our results suggest that novel sulfonamide analogs have anti-metastatic activity in breast and melanoma cancer cell lines and may be used as therapeutic agents to treat malignant cancer. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.12.093

文献信息

• Pyrazolo pyridine derivatives as NADPH oxidase inhibitors
  申请人：GENKYO TEX SA

  公开号：EP2166010A1

  公开（公告）日：2010-03-24

  The present invention is related to pyrazolo pyridine derivatives of Formula (I), pharmaceutical composition thereof and to their use for the treatment and/or prophylaxis of disorders or conditions related to Nicotinamide adenine dinucleotide phosphate oxidase (NADPH Oxidase).

  本发明涉及式(I)的吡唑吡啶衍生物，其药物组成物以及它们用于治疗和/或预防与烟酰胺腺嘌呤二核苷酸磷酸氧化酶（NADPH氧化酶）相关的疾病或症状的用途。
• PYRAZOLO PYRIDINE DERIVATIVES AS NADPH OXIDASE INHIBITORS
  申请人：Page Patrick

  公开号：US20110269757A1

  公开（公告）日：2011-11-03

  The present invention is related to pyrazolo pyridine derivatives of Formula (I), pharmaceutical composition thereof and to their use for the treatment and/or prophylaxis of disorders or conditions related to Nicotinamide adenine dinucleotide phosphate oxidase (NADPH Oxidase).

  本发明涉及式（I）的吡唑吡啶衍生物，其制药组合物以及它们用于治疗和/或预防与尼克酰胺腺嘌呤二核苷酸磷酸氧化酶（NADPH氧化酶）有关的疾病或症状的用途。
• Chemical mechanical planarization for tungsten-containing substrates
  申请人：AIR PRODUCTS AND CHEMICALS, INC.

  公开号：EP2779217A2

  公开（公告）日：2014-09-17

  Chemical mechanical polishing (CMP) compositions for polishing tungsten or tungsten-containing substrates comprise an abrasive, at least one solid catalyst, a chemical additive selected from the groups consisting of piperazine derivatives, salts of cyanate, and combinations thereof; and a liquid carrier. Systems and processes use the aqueous formulations for polishing tungsten or tungsten-containing substrates.

  用于抛光钨或含钨基材的化学机械抛光（CMP）组合物包括磨料、至少一种固体催化剂、一种选自哌嗪衍生物、氰酸盐及其组合的化学添加剂；以及一种液体载体。系统和工艺使用水性制剂抛光钨或含钨基材。
• First in Class, Potent, and Orally Bioavailable NADPH Oxidase Isoform 4 (Nox4) Inhibitors for the Treatment of Idiopathic Pulmonary Fibrosis
  作者：Benoı̂t Laleu、Francesca Gaggini、Mike Orchard、Laetitia Fioraso-Cartier、Laurène Cagnon、Sophie Houngninou-Molango、Angelo Gradia、Guillaume Duboux、Cédric Merlot、Freddy Heitz、Cédric Szyndralewiez、Patrick Page

  DOI：10.1021/jm100773e

  日期：2010.11.11

  We describe the design, synthesis, and optimization of first-in-class series of inhibitors of NADPH oxidase isoform 4 (Nox4), an enzyme implicated in several pathologies, in particular idiopathic pulmonary fibrosis, a life-threatening and orphan disease. Initially, several moderately potent pyrazolopyridine dione derivatives were found during a high-throughput screening campaign. SA R investigation around the pyrazolopyridine dione core led to the discovery of several double-digit nanomolar inhibitors in cell free assays of reactive oxygen species (ROS) production, showing high potency on Nox4 and Nox1. The compounds have little affinity for Nox2 isoform and are selective for Nox4/1 isoforms. The specificity of these compounds was confirmed in an extensive in vitro pharmacological profile, as well as in a counterscreening assay for potential ROS scavenging. Concomitant benefits are good oral bioavailability and high plasma concentrations in vivo, allowing further clinical trials for the potential treatment of fibrotic diseases, cancers, and cardiovascular and metabolic diseases.
• US20140273458A1
  申请人：——

  公开号：US20140273458A1

  公开（公告）日：2014-09-18