4,5-二氨基-6-氯-3-甲基吡啶 | 18232-91-2

• 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
• 中文名称: 4,5-二氨基-6-氯-3-甲基吡啶
• 英文名称: 4,5-diamino-6-chloro-3-methylpyridine
• 英文别名: 2-Chloro-5-methylpyridine-3,4-diamine
• CAS: 18232-91-2
• 化学式: C₆H₈ClN₃
• mdl: MFCD09953778
• 分子量: 157.603
• InChiKey: BLARZXAWOHCFBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  64.9
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2933399090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302

反应信息

• 作为反应物：
  描述：

  4,5-二氨基-6-氯-3-甲基吡啶 在 甲酸 、 偶氮二甲酸二叔丁酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 生成 3-[(1S)-5-bromo-2,3-dihydro-1H-inden-1-yl]-2-ethyl-7-methyl-5H-imidazo[4,5-c]pyridin-4-one
  参考文献：
  名称：

  Design, synthesis, and evaluation of imidazo[4,5-c]pyridin-4-one derivatives with dual activity at angiotensin II type 1 receptor and peroxisome proliferator-activated receptor-γ

  摘要：

  Identification of a series of imidazo[4,5-c]pyridin-4-one derivatives that act as dual angiotensin II type 1 (AT1) receptor antagonists and peroxisome proliferator-activated receptor-gamma (PPAR gamma) partial agonists is described. Starting from a known AT1 antagonist template, conformational restriction was introduced by incorporation of an indane ring that when combined with appropriate substitution at the imidazo[4,5-c]pyridin-4-one provided novel series 5 possessing the desired dual activity. The mode of interaction of this series with PPAR gamma was corroborated through the X-ray crystal structure of 12b bound to the human PPAR gamma ligand binding domain. Modulation of activity at both receptors through substitution at the pyridone nitrogen led to the identification of potent dual AT1 antagonists/PPAR gamma partial agonists. Among them, 21b was identified possessing potent dual pharmacology (AT1 IC50 = 7 nM; PPAR gamma EC50 = 295 nM, 27% max) and good ADME properties. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.088
• 作为产物：
  描述：

  3-甲基-4-硝基吡啶-N-氧化物 在 镍 盐酸 、 硫酸 、 氢气 、 硝酸 、 四氯化锡 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、448.16 kPa 条件下， 反应 4.75h， 生成 4,5-二氨基-6-氯-3-甲基吡啶
  参考文献：
  名称：

  抗固定的3-甲基-3-脱氮基-2'-脱氧腺苷和其他3H-咪唑并[4,5-c]吡啶类似物的合成。

  摘要：

  围绕糖苷键的杂环碱基的旋转允许在核苷中形成顺式和反式构象。主要在DNA双链体中的嘌呤-嘌呤错配中观察到了顺式构象。这样的错配在基于DNA的诊断中引起假阳性寡核苷酸杂交。在这里，我们描述了2'-脱氧腺苷类似物的合成，该类似物保留了其Watson-Crick官能团，但不能形成syn构象。在该类似物中，2'-脱氧腺苷的N3原子被C-CH3基团取代，得到7-甲基-1-β-D-脱氧呋喃核糖基-1H-咪唑并[4,5-c]吡啶-4-基胺或3-甲基-3-deaza-2'-脱氧腺苷（3mddA）。这种修饰在空间上阻止了顺式构象，并且3mddA成为2'-脱氧腺苷的抗固定核苷类似物。

  DOI：

  10.1081/ncn-120016477

文献信息

• IMIDAZOPYRIDINE COMPOUNDS, COMPOSITIONS AND METHODS OF USE
  申请人：Lai Yingjie

  公开号：US20130096104A1

  公开（公告）日：2013-04-18

  The invention provides compounds of Formulas Ia-Ib, stereoisomers or pharmaceutically acceptable salts thereof, wherein A, X, R 1 , R 2 , R 4 , R 5 and R 16 are defined herein, a pharmaceutical composition that includes a compound of Formulas Ia-Ib and a pharmaceutically acceptable carrier, adjuvant or vehicle, and methods of using the compound or composition in therapy, as an inhibitor of TYK2 kinase and conditions related, such as inflammatory illnesses, inflammatory bowel disease or psoriasis.

  本发明提供了公式Ia-Ib的化合物、立体异构体或其药学上可接受的盐，其中A、X、R1、R2、R4、R5和R16在此定义，一种包括公式Ia-Ib化合物和药学上可接受的载体、佐剂或车载物的药物组合物，以及使用该化合物或组合物作为TYK2激酶的抑制剂和相关疾病的治疗方法，例如炎症性疾病、炎症性肠病或牛皮癣。
• Design, synthesis, and evaluation of imidazo[4,5-c]pyridin-4-one derivatives with dual activity at angiotensin II type 1 receptor and peroxisome proliferator-activated receptor-γ
  作者：Agustin Casimiro-Garcia、Ronald J. Heemstra、Christopher F. Bigge、Jing Chen、Fred A. Ciske、Jo Ann Davis、Teresa Ellis、Nadia Esmaeil、Declan Flynn、Seungil Han、Mehran Jalaie、Jeffrey F. Ohren、Noel A. Powell

  DOI：10.1016/j.bmcl.2012.11.088

  日期：2013.2

  Identification of a series of imidazo[4,5-c]pyridin-4-one derivatives that act as dual angiotensin II type 1 (AT1) receptor antagonists and peroxisome proliferator-activated receptor-gamma (PPAR gamma) partial agonists is described. Starting from a known AT1 antagonist template, conformational restriction was introduced by incorporation of an indane ring that when combined with appropriate substitution at the imidazo[4,5-c]pyridin-4-one provided novel series 5 possessing the desired dual activity. The mode of interaction of this series with PPAR gamma was corroborated through the X-ray crystal structure of 12b bound to the human PPAR gamma ligand binding domain. Modulation of activity at both receptors through substitution at the pyridone nitrogen led to the identification of potent dual AT1 antagonists/PPAR gamma partial agonists. Among them, 21b was identified possessing potent dual pharmacology (AT1 IC50 = 7 nM; PPAR gamma EC50 = 295 nM, 27% max) and good ADME properties. (c) 2012 Elsevier Ltd. All rights reserved.
• THE SYNTHESIS OF<i>ANTI</i>-FIXED 3-METHYL-3- DEAZA-2′-DEOXYADENOSINE AND OTHER 3<i>H</i>-IMIDAZO[4,5-c]PYRIDINE ANALOGS
  作者：Rostem J. Irani、John SantaLucia

  DOI：10.1081/ncn-120016477

  日期：2002.12.31

  syn and anti conformations in nucleosides. The syn conformation has been observed primarily in purine-purine mismatches in DNA duplexes. Such mismatches give rise to false positive oligonucleotide hybridization in DNA-based diagnostics. Here we describe the synthesis of an analog of 2'-deoxyadenosine that retains its Watson-Crick functional groups, but cannot form the syn conformation. In this analog

  围绕糖苷键的杂环碱基的旋转允许在核苷中形成顺式和反式构象。主要在DNA双链体中的嘌呤-嘌呤错配中观察到了顺式构象。这样的错配在基于DNA的诊断中引起假阳性寡核苷酸杂交。在这里，我们描述了2'-脱氧腺苷类似物的合成，该类似物保留了其Watson-Crick官能团，但不能形成syn构象。在该类似物中，2'-脱氧腺苷的N3原子被C-CH3基团取代，得到7-甲基-1-β-D-脱氧呋喃核糖基-1H-咪唑并[4,5-c]吡啶-4-基胺或3-甲基-3-deaza-2'-脱氧腺苷（3mddA）。这种修饰在空间上阻止了顺式构象，并且3mddA成为2'-脱氧腺苷的抗固定核苷类似物。