4-methyl-N'-[(1E)-pyridin-2-ylmethylene]benzenesulfonohydrazide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-methyl-N'-[(1E)-pyridin-2-ylmethylene]benzenesulfonohydrazide
• 英文别名: (E)-4-methyl-N'-(pyridin-2-ylmethylene)benzenesulfonohydrazide；4-Methyl-N-[(E)-pyridin-2-ylmethylideneamino]benzenesulfonamide
• 化学式: C₁₃H₁₃N₃O₂S
• 分子量: 275.331
• InChiKey: BONWWPOKZVRKEL-XNTDXEJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  79.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-methyl-N'-[(1E)-pyridin-2-ylmethylene]benzenesulfonohydrazide 在 吗啉 作用下， 以83.3 %的产率得到1,2,3-噻唑(1,5-a)吡啶
  参考文献：
  名称：

  [EN] COMPOUNDS, COMPOSITIONS AND METHODS OF USE
  [FR] COMPOSÉS, COMPOSITIONS ET PROCÉDÉS D'UTILISATION ASSOCIÉS

  摘要：

  Herein, compounds, compositions and methods for modulating inclusion formation and stress granules in cells related to the onset of neurodegenerative diseases, musculoskeletal diseases, cancer, ophthalmological diseases, and viral infections are described.

  公开号：

  WO2023060173A1
• 作为产物：
  描述：

  吡啶-2-甲醛 、 对甲苯磺酰肼 以 乙醇 为溶剂， 生成 4-methyl-N'-[(1E)-pyridin-2-ylmethylene]benzenesulfonohydrazide
  参考文献：
  名称：

  2-（2- [3-（吡啶-3-基氧基）苯基] -2H-四唑-5-基）吡啶：一种高效，口服活性，代谢型谷氨酸亚型5（mGlu5）受体拮抗剂。

  摘要：

  对3-（5-吡啶-2-基-2H-四唑-2-基）苄腈2的构效关系的研究导致了2-（2- [3-（吡啶-3-基氧基）苯基]-的发现。 2H-四唑-5-基）吡啶（10）-一种高效且选择性的mGlu5受体拮抗剂，在大鼠和跨物种口服生物利用度中具有良好的脑部渗透性和体内受体占有率。

  DOI：

  10.1016/j.bmcl.2004.09.012

文献信息

• 3-[Substituted]-5-(5-pyridin-2-yl-2H-tetrazol-2-yl)benzonitriles: Identification of highly potent and selective metabotropic glutamate subtype 5 receptor antagonists
  作者：Lida R. Tehrani、Nicholas D. Smith、Dehua Huang、Steve F. Poon、Jeffrey R. Roppe、Thomas Jon Seiders、Deborah F. Chapman、Janice Chung、Merryl Cramer、Nicholas D.P. Cosford

  DOI：10.1016/j.bmcl.2005.07.062

  日期：2005.11

  3-position led to a substantial increase in in vitro potency. In particular, 3-fluoro-5-(5-pyridin-2-yl-2H-tetrazol-2-yl)benzonitrile (7) is a highly potent and selective mGlu5 receptor antagonist with good rat pharmacokinetics, brain penetration, and in vivo receptor occupancy.

  对3-（5-吡啶-2--2-基-2H-四唑-2-基）苄腈2的苯环的构效关系研究导致发现在3-位的小的非氢键供体取代基大大提高了体外效能。特别是3-氟-5-（5-吡啶-2-基-2H-四唑-2-基）苄腈（7）是一种高效且选择性的mGlu5受体拮抗剂，具有良好的大鼠药代动力学，脑渗透性和体内活性受体占用。
• Discovery of Novel Heteroarylazoles That Are Metabotropic Glutamate Subtype 5 Receptor Antagonists with Anxiolytic Activity
  作者：Jeffrey Roppe、Nicholas D. Smith、Dehua Huang、Lida Tehrani、Bowei Wang、Jeffrey Anderson、Jesse Brodkin、Janice Chung、Xiaohui Jiang、Christopher King、Benito Munoz、Mark A. Varney、Petpiboon Prasit、Nicholas D. P. Cosford

  DOI：10.1021/jm049828c

  日期：2004.9.1

  The highly potent, selective, and brain-penetrant metabotropic glutamate subtype 5 (mGlu5) receptor antagonists 3-(5-pyridin-2-yl-2H-tetrazol-2-yl)benzonitrile (47) and 3-fluoro-5-(5-pyridin-2-yl-2H-tetrazol-2-yl)benzonitrile (48) are reported. Compound 47 is active in the rat fear-potentiated startle (FPS) model of anxiety with ED50 = 5.4 mg/kg (po) when dosed acutely. In this model the anxiolytic effects of 47 rapidly tolerate on repeated dosing.
• 3-[3-Fluoro-5-(5-pyridin-2-yl-2H-tetrazol-2-yl)phenyl]-4-methylpyridine: a highly potent and orally bioavailable metabotropic glutamate subtype 5 (mGlu5) receptor antagonist
  作者：Steve F. Poon、Brian W. Eastman、Deborah F. Chapman、Janice Chung、Merryl Cramer、Gregory Holtz、Nicholas D.P. Cosford、Nicholas D. Smith

  DOI：10.1016/j.bmcl.2004.09.011

  日期：2004.11

  Structure-activity relationship studies performed around 3-fluoro-5-(5-pyridin-2-yl-2H-tetrazol-2-yl)benzonitrile for the purpose of developing novel mGlu5 receptor antagonists are described. Synthesis of a series of four-ring tetrazoles led to the discovery of 3-[3-fluoro-5-(5-pyridin-2-yl-2H-tetrazol-2-yl)phenyl]-4-methylpyridine, a highly potent, brain penetrant, azole-based mGlu5 receptor antagonist. (C) 2004 Elsevier Ltd. All rights reserved.
• Discovery of highly potent, selective, orally bioavailable, metabotropic glutamate subtype 5 (mGlu5) receptor antagonists devoid of cytochrome P450 1A2 inhibitory activity
  作者：Nicholas D. Smith、Steve F. Poon、Dehua Huang、Mitchell Green、Christopher King、Lida Tehrani、Jeffrey R. Roppe、Janice Chung、Deborah P. Chapman、Merryl Cramer、Nicholas D.P. Cosford

  DOI：10.1016/j.bmcl.2004.09.018

  日期：2004.11

  Structure-activity relationship studies focused on bio-isosteric replacements of 2-pyridyl resulted in mGlu5 receptor antagonists with reduced inhibition of cytochrome P450 1A2. This led to highly potent, selective and orally bioavailable 2-imidazolyl tetrazoles such as (10) that are devoid of cytochrome P450 inhibitory activity. (C) 2004 Elsevier Ltd. All rights reserved.
• SAITO, KATSUHIRO;ISHIHARA, HIRAKU, HETEROCYCLES, 26,(1987) N 7, 1891-1898
  作者：SAITO, KATSUHIRO、ISHIHARA, HIRAKU

  DOI：——

  日期：——