4-(chloromethyl)-N-(pyridin-2-yl)benzamide | 405058-28-8

• 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-(chloromethyl)-N-(pyridin-2-yl)benzamide
• 英文别名: 4-(chloromethyl)-N-pyridin-2-ylbenzamide
• CAS: 405058-28-8
• 化学式: C₁₃H₁₁ClN₂O
• mdl: MFCD11104980
• 分子量: 246.696
• InChiKey: GOTAPEHQHUVRTD-UHFFFAOYSA-N

物化性质

• 沸点：
  340.9±27.0 °C(Predicted)
• 密度：
  1.303±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.076
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-nitro-N-(5,6,7,8-tetrahydro-quinolin-8-yl)-benzenesulfonamide 、 4-(chloromethyl)-N-(pyridin-2-yl)benzamide 在 potassium carbonate 、 potassium iodide 作用下， 以 乙腈 为溶剂， 以92%的产率得到4-{[(2-Nitrobenzenesulfonyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-N-pyridin-2-yl-benzamide
  参考文献：
  名称：

  Discovery of Novel Small Molecule Orally Bioavailable C−X−C Chemokine Receptor 4 Antagonists That Are Potent Inhibitors of T-Tropic (X4) HIV-1 Replication

  摘要：

  The redesign of azamacrocyclic CXCR4 chemokine receptor antagonists resulted in the discovery of novel, small molecule, orally bioavailable compounds that retained T-tropic (CXCR4 using, X4) anti-HIV-1 activity. A structure activity relationship (SA R) was determined on the basis of the inhibition of replication of X4 HIV-1 NL4.3 in MT-4 cells. As a result of lead optimization, we identified (S)-N'-((1H-benzo[d]imidazol-2-Amethyl)-N'-(5,6,7,8-tetrahydroquinolin-8-yl)butane-1,4-diamine (AMD070) 2 as a potent and selective antagonist of CXCR4 with an IC(50) value of 13 nM in a CXCR4 (125)I-SDF inhibition binding assay. Compound 2 inhibited the replication of T-tropic HIV-1 (NL4.3 strain) in MT-4 cells and PBMCs with an IC(50) of 2 and 26 nM, respectively, while remaining noncytotoxic to cells at concentrations exceeding 23 mu M. The pharmacokinetics of 2 was evaluated in rat and dog, and good oral bioavailability was observed in both species. This compound represents the first small molecule orally bioavailable CXCR4 antagonist that was developed for the treatment of HIV-1 infection.

  DOI：

  10.1021/jm100073m
• 作为产物：
  描述：

  2-氨基吡啶 、 4-氯甲基苯甲酰氯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以49%的产率得到4-(chloromethyl)-N-(pyridin-2-yl)benzamide
  参考文献：
  名称：

  Discovery of Novel Small Molecule Orally Bioavailable C−X−C Chemokine Receptor 4 Antagonists That Are Potent Inhibitors of T-Tropic (X4) HIV-1 Replication

  摘要：

  The redesign of azamacrocyclic CXCR4 chemokine receptor antagonists resulted in the discovery of novel, small molecule, orally bioavailable compounds that retained T-tropic (CXCR4 using, X4) anti-HIV-1 activity. A structure activity relationship (SA R) was determined on the basis of the inhibition of replication of X4 HIV-1 NL4.3 in MT-4 cells. As a result of lead optimization, we identified (S)-N'-((1H-benzo[d]imidazol-2-Amethyl)-N'-(5,6,7,8-tetrahydroquinolin-8-yl)butane-1,4-diamine (AMD070) 2 as a potent and selective antagonist of CXCR4 with an IC(50) value of 13 nM in a CXCR4 (125)I-SDF inhibition binding assay. Compound 2 inhibited the replication of T-tropic HIV-1 (NL4.3 strain) in MT-4 cells and PBMCs with an IC(50) of 2 and 26 nM, respectively, while remaining noncytotoxic to cells at concentrations exceeding 23 mu M. The pharmacokinetics of 2 was evaluated in rat and dog, and good oral bioavailability was observed in both species. This compound represents the first small molecule orally bioavailable CXCR4 antagonist that was developed for the treatment of HIV-1 infection.

  DOI：

  10.1021/jm100073m

文献信息

• Aromatic amine derivative and use thereof
  申请人：Taniguchi Takahiko

  公开号：US20090325956A1

  公开（公告）日：2009-12-31

  The present invention provides a novel SCD inhibitor. An SCD inhibitor containing a compound represented by the formula [I] wherein ring A is an optionally substituted aromatic ring, ring B is an optionally substituted ring, ring C is an optionally substituted aromatic ring, R is a hydrogen atom, an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group, and X is a spacer having 1 to 5 atoms in the main chain, or a salt thereof, or a prodrug thereof.

  本发明提供了一种新型SCD抑制剂。一种包含由下式[I]表示的化合物的SCD抑制剂 其中环A是可选择取代的芳香环，环B是可选择取代的环，环C是可选择取代的芳香环，R是氢原子，可选择取代的碳氢基团或可选择取代的杂环基团，X是具有主链中1到5个原子的间隔物，或其盐，或其前药。
• NEW HISTONE DEACETYLASE INHIBITORS BASED SIMULTANEOUSLY ON TRISUBSTITUTED 1H-PYRROLES AND AROMATIC AND HETEROAROMATIC SPACERS
  申请人：Cossío Mora Fernando Pedro

  公开号：US20120196885A1

  公开（公告）日：2012-08-02

  The present invention refers to compounds derived from trisubstituted 1H-pyrrole rings and aromatic rings, which have the following formula (I): wherein: R 1 and R 2 represent, independently, an optionally substituted C 6 -C 10 aryl radical or an optionally substituted heteroaryl radical; A and M represent, independently, a methylene group or a single bond, in which case the adjacent aromatic ring would be attached directly to the amide group; the Y═Z group represents together and indistinctly an oxygen atom, a sulfur atom, a cis-vinylidene group, an imino group, or a methine group with a sp 2 -hybridized carbon atom; X represents indistinctly a methine group, a cis-vinylidene group or a nitrogen atom; and W represents a hydroxyl group, an optionally substituted C 1 -C 6 alkyl group, an optionally substituted heteroaryl group or an optionally substituted C 6 -C 10 aryl group; or a salt, solvate or prodrug thereof, as well as to the process for their preparation and the use thereof for the treatment of cancer.

  本发明涉及从三取代的1H-吡咯环和芳香环衍生的化合物，其具有以下公式（I）： 其中： R1和R2分别表示一个可选择取代的C6-C10芳基基团或一个可选择取代的杂环基团； A和M分别表示一个亚甲基基团或一个单键，此时相邻的芳香环将直接连接到酰胺基团； Y═Z基团一起表示一个氧原子、硫原子、顺式-乙烯基团、亚胺基团或具有sp2杂化碳原子的甲基基团； X不明确地表示一个甲基基团、顺式-乙烯基团或一个氮原子； W表示一个羟基、一个可选择取代的C1-C6烷基基团、一个可选择取代的杂环基团或一个可选择取代的C6-C10芳基基团； 或其盐、溶剂合物或前药，以及其制备方法和用于治疗癌症的用途。
• Discovery of Novel Small Molecule Orally Bioavailable C−X−C Chemokine Receptor 4 Antagonists That Are Potent Inhibitors of T-Tropic (X4) HIV-1 Replication
  作者：Renato T. Skerlj、Gary J. Bridger、Al Kaller、Ernest J. McEachern、Jason B. Crawford、Yuanxi Zhou、Bem Atsma、Jonathon Langille、Susan Nan、Duane Veale、Trevor Wilson、Curtis Harwig、Sigrid Hatse、Katrien Princen、Erik De Clercq、Dominique Schols

  DOI：10.1021/jm100073m

  日期：2010.4.22

  The redesign of azamacrocyclic CXCR4 chemokine receptor antagonists resulted in the discovery of novel, small molecule, orally bioavailable compounds that retained T-tropic (CXCR4 using, X4) anti-HIV-1 activity. A structure activity relationship (SA R) was determined on the basis of the inhibition of replication of X4 HIV-1 NL4.3 in MT-4 cells. As a result of lead optimization, we identified (S)-N'-((1H-benzo[d]imidazol-2-Amethyl)-N'-(5,6,7,8-tetrahydroquinolin-8-yl)butane-1,4-diamine (AMD070) 2 as a potent and selective antagonist of CXCR4 with an IC(50) value of 13 nM in a CXCR4 (125)I-SDF inhibition binding assay. Compound 2 inhibited the replication of T-tropic HIV-1 (NL4.3 strain) in MT-4 cells and PBMCs with an IC(50) of 2 and 26 nM, respectively, while remaining noncytotoxic to cells at concentrations exceeding 23 mu M. The pharmacokinetics of 2 was evaluated in rat and dog, and good oral bioavailability was observed in both species. This compound represents the first small molecule orally bioavailable CXCR4 antagonist that was developed for the treatment of HIV-1 infection.