N²,N⁴-diisopentyl-6-(1-((4,5-diphenyloxazol-2-yl)methyl)-1H-1,2,3-triazol-4-yl)-1,3,5-triazine-2,4-diamine | 1421369-19-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N²,N⁴-diisopentyl-6-(1-((4,5-diphenyloxazol-2-yl)methyl)-1H-1,2,3-triazol-4-yl)-1,3,5-triazine-2,4-diamine
• 英文别名: 6-[1-[(4,5-diphenyl-1,3-oxazol-2-yl)methyl]triazol-4-yl]-2-N,4-N-bis(3-methylbutyl)-1,3,5-triazine-2,4-diamine
• CAS: 1421369-19-8
• 化学式: C₃₁H₃₇N₉O
• 分子量: 551.694
• InChiKey: ABPXHHVUUQYNIC-UHFFFAOYSA-N

物化性质

• 沸点：
  728.5±70.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  41
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  120
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2-(chloromethyl)-4,5-diphenyloxazole 在 sodium azide 、 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 N²,N⁴-diisopentyl-6-(1-((4,5-diphenyloxazol-2-yl)methyl)-1H-1,2,3-triazol-4-yl)-1,3,5-triazine-2,4-diamine
  参考文献：
  名称：

  1,2,3-Triazole-based inhibitors of Porphyromonas gingivalis adherence to oral streptococci and biofilm formation

  摘要：

  The development and use of small-molecule inhibitors of the adherence of Porphyromonas gingivalis to oral streptococci represents a potential therapy for the treatment of periodontal disease as these organisms work in tandem to colonize the oral cavity. Earlier work from these laboratories demonstrated that a small synthetic peptide was an effective inhibitor of the interaction between P. gingivalis and Streptococcus gordonii and that a small-molecule peptidomimetic would provide a more stable, less expensive and more effective inhibitor. An array of 2-(azidomethyl)- and 2-(azidophenyl)-4,5-diaryloxazoles having a full range of hydrophobic groups were prepared and reacted with substituted arylacetylenes to afford the corresponding 'click' products. The title compounds were evaluated for their ability to inhibit P. gingivalis' adherence to oral streptococci and several were found to be inhibitory in the range of (IC50) 5.3-67 mu M. (C) 2016 The Authors. Published by Elsevier Ltd. This is an open access article under the CC BY-NC-ND license (http://creativecommons.orgilicensesiby-nc-nd/4.0/).

  DOI：

  10.1016/j.bmc.2016.08.059

文献信息

• [EN] ANTI-BIOFILM COMPOUNDS<br/>[FR] COMPOSÉS ANTI-BIOFILM
  申请人：UNIV LOUISVILLE RES FOUND

  公开号：WO2013016206A1

  公开（公告）日：2013-01-31

  The present invention provides non-peptide compounds of formula (I) wherein: X is -(C1-C8)allcyl-, aryl or -aryl(C1-C8)alkyl-; Y is -(C1-C8)alkyl- or absent; W is heteroaryl, (C3-C7)carbocycle or aryl, wherein any heteroaryl, (C3-C7)carbocycle or, aryl of W is optionally substituted with one or more (e.g. 1, 2, 3, 4 or 5) Z1 groups; R1 is (C1-C8)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl or aryl, wherein aryl is optionally substituted with one or more (e.g. 1, 2, 3, 4 or 5) groups selected from (C1-C8)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C3-C7)carbocycle, halo(C1-C3)alkyl, -CN, NO2, halogen, -ORa, -SRa, -S(O)2NRbRc, -NRbRc, -NRaCORd, -C(O)Ra, -C(O)ORa, and -C(O)NRbRc; R2 is (C1-C8)alkyl, (C2-C8)alkenyl, (C2-C8)Jalkynyl or aryl, wherein aryl is optionally substituted with one or more (e.g. 1, 2, 3, 4 or 5) groups selected from (C1-C8)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C3-C7)carbocycle, halo(C1-C3)alkyl, -CN, NO2, halogen, -ORe, -SRe, -S(O)2NRfRg, -NRfRg -NReCORh, -C(O)Re, -C(O)ORe and -C(O)NRfRg; I that mimic the streptococcal; SspB Adherence Region (BAR) and function as inhibitors of P. gingivalis adherence to streptococci. The invention also provides methods of making and using the inhibitors.

  本发明提供了式(I)的非肽化合物，其中：X为-(C1-C8)烷基，芳基或-芳基(C1-C8)烷基-；Y为-(C1-C8)烷基或不存在；W为杂环芳基，(C3-C7)碳环或芳基，其中W的任何杂环芳基，(C3-C7)碳环或芳基可以选择性地用一个或多个(Z1)基团取代；R1为(C1-C8)烷基，(C2-C8)烯基，(C2-C8)炔基或芳基，其中芳基可以选择性地用一个或多个(C1-C8)烷基，(C2-C8)烯基，(C2-C8)炔基，(C3-C7)碳环，卤代(C1-C3)烷基，-CN，NO2，卤素，-ORa，-SRa，-S(O)2NRbRc，-NRbRc，-NRaCORd，-C(O)Ra，-C(O)ORa和-C(O)NRbRc基团中的一个或多个取代；R2为(C1-C8)烷基，(C2-C8)烯基，(C2-C8)炔基或芳基，其中芳基可以选择性地用一个或多个(C1-C8)烷基，(C2-C8)烯基，(C2-C8)炔基，(C3-C7)碳环，卤代(C1-C3)烷基，-CN，NO2，卤素，-ORe，-SRe，-S(O)2NRfRg，-NRfRg，-NReCORh，-C(O)Re，-C(O)ORe和-C(O)NRfRg基团中的一个或多个取代；I模拟链球菌SspB粘附区（BAR）并作为P. gingivalis粘附于链球菌的抑制剂。该发明还提供了制备和使用这些抑制剂的方法。
• ANTI-BIOFILM COMPOUNDS
  申请人：Demuth Donald R.

  公开号：US20140161845A1

  公开（公告）日：2014-06-12

  The present invention provides non-peptide compounds of formula (I) wherein: X is —(C 1 -C 8 )allcyl-, aryl or -aryl(C 1 -C 8 )alkyl-; Y is —(C 1 -C 8 )alkyl- or absent; W is heteroaryl, (C 3 -C 7 )carbocycle or aryl, wherein any heteroaryl, (C 3 -C 7 )carbocycle or, aryl of W is optionally substituted with one or more (e.g. 1, 2, 3, 4 or 5) Z 1 groups; R 1 is (C 1 -C 8 )alkyl, (C 2 -C 8 )alkenyl, (C 2 -C 8 )alkynyl or aryl, wherein aryl is optionally substituted with one or more (e.g. 1, 2, 3, 4 or 5) groups selected from (C 1 -C 8 )alkyl, (C 2 -C 8 )alkenyl, (C 2 -C 8 )alkynyl, (C 3 -C 7 )carbocycle, halo(C 1 -C 3 )alkyl, —CN, NO 2 , halogen, —OR a , —SR a , —S(O) 2 NR b R c , —NR b R c , —NR a COR d , —C(O)R a , —C(O)OR a , and —C(O)NR b R c ; R 2 is (C 1 -C 8 )alkyl, (C 2 -C 8 )alkenyl, (C 2 -C 8 )Jalkynyl or aryl, wherein aryl is optionally substituted with one or more (e.g. 1, 2, 3, 4 or 5) groups selected from (C 1 -C 8 )alkyl, (C 2 -C 8 )alkenyl, (C 2 -C 8 )alkynyl, (C 3 -C 7 )carbocycle, halo(C 1 -C 3 )alkyl, —CN, NO 2 , halogen, —OR e , —SR e , —S(O) 2 NR f R g , —NR f R g —NR e COR h , —C(O)R e , —C(O)OR e and —C(O)NR f R g ; I that mimic the streptococcal; SspB Adherence Region (BAR) and function as inhibitors of P. gingivalis adherence to streptococci. The invention also provides methods of making and using the inhibitors.

  本发明提供了化合物(I)的非肽类衍生物，其中：X是—(C1-C8)烷基，芳基或-芳基(C1-C8)烷基-; Y是—(C1-C8)烷基或不存在; W是杂环芳基，(C3-C7)碳环或芳基，其中W的任何杂环芳基，(C3-C7)碳环或芳基可选择地用一个或多个(Z1)基团取代; R1是(C1-C8)烷基，(C2-C8)烯基，(C2-C8)炔基或芳基，其中芳基可选择地用一个或多个(C1-C8)烷基，(C2-C8)烯基，(C2-C8)炔基，(C3-C7)碳环，卤代(C1-C3)烷基，—CN，NO2，卤素，—ORa，—SRa，—S(O)2NRbRc，—NRbRc，—NRaCORd，—C(O)Ra，—C(O)ORa和—C(O)NRbRc基团中的一个或多个取代; R2是(C1-C8)烷基，(C2-C8)烯基，(C2-C8)炔基或芳基，其中芳基可选择地用一个或多个(C1-C8)烷基，(C2-C8)烯基，(C2-C8)炔基，(C3-C7)碳环，卤代(C1-C3)烷基，—CN，NO2，卤素，—ORe，—SRe，—S(O)2NRfRg，—NRfRg—NReCORh，—C(O)Re，—C(O)ORe和—C(O)NRfRg基团中的一个或多个取代; I模拟链球菌SspB粘附区(BAR)，并作为P. gingivalis粘附到链球菌的抑制剂。本发明还提供制备和使用抑制剂的方法。
• US9167820B2
  申请人：——

  公开号：US9167820B2

  公开（公告）日：2015-10-27
• 1,2,3-Triazole-based inhibitors of Porphyromonas gingivalis adherence to oral streptococci and biofilm formation
  作者：Pravin C. Patil、Jinlian Tan、Donald R. Demuth、Frederick A. Luzzio

  DOI：10.1016/j.bmc.2016.08.059

  日期：2016.11

  The development and use of small-molecule inhibitors of the adherence of Porphyromonas gingivalis to oral streptococci represents a potential therapy for the treatment of periodontal disease as these organisms work in tandem to colonize the oral cavity. Earlier work from these laboratories demonstrated that a small synthetic peptide was an effective inhibitor of the interaction between P. gingivalis and Streptococcus gordonii and that a small-molecule peptidomimetic would provide a more stable, less expensive and more effective inhibitor. An array of 2-(azidomethyl)- and 2-(azidophenyl)-4,5-diaryloxazoles having a full range of hydrophobic groups were prepared and reacted with substituted arylacetylenes to afford the corresponding 'click' products. The title compounds were evaluated for their ability to inhibit P. gingivalis' adherence to oral streptococci and several were found to be inhibitory in the range of (IC50) 5.3-67 mu M. (C) 2016 The Authors. Published by Elsevier Ltd. This is an open access article under the CC BY-NC-ND license (http://creativecommons.orgilicensesiby-nc-nd/4.0/).