4-azido-N-benzylbenzamide

• 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-azido-N-benzylbenzamide
• 化学式: C₁₄H₁₂N₄O
• 分子量: 252.275
• InChiKey: CDULCIWWEBFPFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  43.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-azido-N-benzylbenzamide 在 噻吩-2-甲酸亚铜(I) 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 17.0h， 生成
  参考文献：
  名称：

  A comparison of novel organoiridium(III) complexes and their ligands as a potential treatment for prostate cancer

  摘要：

  A range of 1,4-substituted 2-pyridyl-N-phenyl triazoles were synthesised and evaluated for their anti proliferative properties against lymph node cancer of the prostate (LNCaP) and bone metastasis of prostate cancer (PC-3) cells. Excellent-to-low IC50 values were determined (5.6-250 mu M), and a representative group of 4 ligands were then complexed to iridium(III) giving highly luminescent species. Re-evaluation of these compounds against both cell lines was then undertaken and improved potency (up to 72-fold) was observed, giving IC50 values of 0.36-11 mu M for LNCaP and 0.85-5.9 mu M for PC-3. Preliminary screens for in vivo toxicity were conducted using a zebrafish model showing a wide range of induced toxicity depending of the compound evaluated. Apoptosis and Caspase-3 levels were also determined and showed no statistical difference between some of the treated specimens and the controls. This study may identify novel therapeutic agents for advanced stage of prostate cancer in humans. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.12.035
• 作为产物：
  描述：

  对氨基苯甲酸 在 盐酸 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 氯仿 、 水 、 乙腈 为溶剂， 反应 3.25h， 生成 4-azido-N-benzylbenzamide
  参考文献：
  名称：

  A comparison of novel organoiridium(III) complexes and their ligands as a potential treatment for prostate cancer

  摘要：

  A range of 1,4-substituted 2-pyridyl-N-phenyl triazoles were synthesised and evaluated for their anti proliferative properties against lymph node cancer of the prostate (LNCaP) and bone metastasis of prostate cancer (PC-3) cells. Excellent-to-low IC50 values were determined (5.6-250 mu M), and a representative group of 4 ligands were then complexed to iridium(III) giving highly luminescent species. Re-evaluation of these compounds against both cell lines was then undertaken and improved potency (up to 72-fold) was observed, giving IC50 values of 0.36-11 mu M for LNCaP and 0.85-5.9 mu M for PC-3. Preliminary screens for in vivo toxicity were conducted using a zebrafish model showing a wide range of induced toxicity depending of the compound evaluated. Apoptosis and Caspase-3 levels were also determined and showed no statistical difference between some of the treated specimens and the controls. This study may identify novel therapeutic agents for advanced stage of prostate cancer in humans. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.12.035

文献信息

• Acyl Fluorides: Fast, Efficient, and Versatile Lysine-Based Protein Conjugation via Plug-and-Play Strategy
  作者：Igor Dovgan、Sylvain Ursuegui、Stéphane Erb、Chloé Michel、Sergii Kolodych、Sarah Cianférani、Alain Wagner

  DOI：10.1021/acs.bioconjchem.7b00141

  日期：2017.5.17

  preparation of functionally enhanced antibodies with a defined average degree of conjugation (DoC). The first stage (plug) allows the controllable and efficient installation of azide groups on lysine residues of a native antibody using 4-azidobenzoyl fluoride. The second step (play) allows for versatile antibody functionalization with a single payload or combination of payloads, such as a toxin, a fluorophore

  我们报告了一种即插即用的策略，用于制备具有确定的平均缀合度（DoC）的功能增强的抗体。第一阶段（塞子）允许使用4-叠氮基苯甲酰氟将叠氮化物基团可控且有效地安装在天然抗体的赖氨酸残基上。第二步（过程）允许通过无铜应变促进的叠氮化物-炔烃环加成反应（SPAAC）使用单个有效载荷或有效载荷的组合（例如毒素，荧光团或寡核苷酸）进行多功能的抗体功能化。值得注意的是，与经典的N-羟基琥珀酰亚胺酯（NHS）策略相比，苯甲酰氟在PBS缓冲液中显示出更快，更有效的赖氨酸残基酰化作用。
• Triazole Derivative and Use Thereof
  申请人：Kubo Keiji

  公开号：US20090105253A1

  公开（公告）日：2009-04-23

  The present invention relates to a thrombin receptor antagonist containing a compound represented by the formula (I) wherein R 1a , R 1b and R 2 are each a hydrogen atom, an optionally substituted hydrocarbon group, an optionally substituted heterocyclic group, or an optionally substituted alkoxy, R 3 is a group represented by the formula —NHCOR 4 , —NHSO 2 R 5 , —NHCON(R 6a )(R 6b ), —NHCOOR 7 or —CONHR 8 wherein R 4 , R 5 , R 6a , R 6b , R 7 and R 8 are each a hydrogen atom, an optionally substituted hydrocarbon group, an optionally substituted heterocyclic group and the like), ring A is monocyclic aromatic ring optionally further having substituent(s), R 1a and R 1b are optionally bonded to each other to form an optionally substituted nitrogen-containing non-aromatic heterocycle, or a salt thereof or a prodrug thereof. The thrombin receptor antagonist of the present invention has a thrombin receptor (particularly PAR-1) antagonistic action and is useful for the prophylaxis or treatment of PAR-1 mediated pathological condition or disease.

  本发明涉及一种含有式(I)所表示的化合物的凝血酶受体拮抗剂，其中R1a、R1b和R2分别是氢原子、可选取代的碳氢基团、可选取代的杂环基团或可选取代的烷氧基，R3是由式—NHCOR4、—NHSO2R5、—NHCON(R6a)(R6b)、—NHCOOR7或—CONHR8所表示的基团，其中R4、R5、R6a、R6b、R7和R8分别是氢原子、可选取代的碳氢基团、可选取代的杂环基团等，环A是单环芳香环，可选地进一步具有取代基，R1a和R1b可选择性地连接在一起形成可选取代的含氮非芳香杂环，或其盐或前药。本发明的凝血酶受体拮抗剂具有凝血酶受体（特别是PAR-1）拮抗作用，可用于预防或治疗PAR-1介导的病理状态或疾病。
• Triazole derivative and use thereof
  申请人：Takeda Pharmaceutical Company Limited

  公开号：US07803822B2

  公开（公告）日：2010-09-28

  The present invention relates to a thrombin receptor antagonist containing a compound represented by the formula (I) wherein R1a, R1b and R2 are each a hydrogen atom, an optionally substituted hydrocarbon group, an optionally substituted heterocyclic group, or an optionally substituted alkoxy, R3 is a group represented by the formula —NHCOR4, —NHSO2R5, —NHCON(R6a)(R6b), —NHCOOR7 or —CONHR8 wherein R4, R5, R6a, R6b, R7 and R8 are each a hydrogen atom, an optionally substituted hydrocarbon group, an optionally substituted heterocyclic group and the like), ring A is monocyclic aromatic ring optionally further having substituent(s), R1a and R1b are optionally bonded to each other to form an optionally substituted nitrogen-containing non-aromatic heterocycle, or a salt thereof or a prodrug thereof. The thrombin receptor antagonist of the present invention has a thrombin receptor (particularly PAR-1) antagonistic action and is useful for the prophylaxis or treatment of PAR-1 mediated pathological condition or disease.

  本发明涉及含有式(I)所表示的化合物的凝血酶受体拮抗剂，其中R1a、R1b和R2分别是氢原子、可选取代的碳氢基团、可选取代的杂环基团或可选取代的烷氧基，R3是由式—NHCOR4、—NHSO2R5、—NHCON(R6a)(R6b)、—NHCOOR7或—CONHR8所表示的基团，其中R4、R5、R6a、R6b、R7和R8分别是氢原子、可选取代的碳氢基团、可选取代的杂环基团等，环A是单环芳香环，可选地进一步具有取代基，R1a和R1b可选地相互连接以形成可选取代的含氮非芳香杂环，或其盐或前药。本发明的凝血酶受体拮抗剂具有凝血酶受体（特别是PAR-1）拮抗作用，可用于预防或治疗PAR-1介导的病理状态或疾病。
• TRIAZOLE DERIVATIVE AND THE USE THEREOF
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP1867331A1

  公开（公告）日：2007-12-19

  The present invention relates to a thrombin receptor antagonist containing a compound represented by the formula (I) wherein R1a, R1b and R2 are each a hydrogen atom, an optionally substituted hydrocarbon group, an optionally substituted heterocyclic group, or an optionally substituted alkoxy, R3 is a group represented by the formula -NHCOR4, -NHSO2R5, -NHCON(R6a) (R6b), -NHCOOR7 or -CONHR8 wherein R4, R5, R6a, R6b, R7 and R8 are each a hydrogen atom, an optionally substituted hydrocarbon group, an optionally substituted heterocyclic group and the like), ring A is monocyclic aromatic ring optionally further having substituent(s), R1a and R1b are optionally bonded to each other to form an optionally substituted nitrogen-containing non-aromatic heterocycle, or a salt thereof or a prodrug thereof. The thrombin receptor antagonist of the present invention has a thrombin receptor (particularly PAR-1) antagonistic action and is useful for the prophylaxis or treatment of PAR-1 mediated pathological condition or disease.

  本发明涉及一种凝血酶受体拮抗剂，其中含有由式（I）代表的化合物 其中 R1a、R1b 和 R2 各为氢原子、任选取代的烃基、任选取代的杂环基团或任选取代的烷氧基，R3 为由式 -NHCOR4、-NHSO2R5、-NHCON(R6a) (R6b)、-NHCOOR7 或 -CONHR8 所代表的基团，其中 R4、R5、R6a、R6b、R7 和 R8 各为氢原子、任选取代的烃基、任选取代的杂环基等），环 A 是单环芳香环，任选进一步具有取代基，R1a 和 R1b 任选相互键合以形成任选取代的含氮非芳香杂环，或其盐或其原药。本发明的凝血酶受体拮抗剂具有凝血酶受体（尤其是 PAR-1）拮抗作用，可用于预防或治疗 PAR-1 介导的病理状态或疾病。
• US7803822B2
  申请人：——

  公开号：US7803822B2

  公开（公告）日：2010-09-28