5-benzyl-4-phenylthiazol-2-amine | 905592-30-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-benzyl-4-phenylthiazol-2-amine
• 英文别名: 4-phenyl-5-(phenylmethyl)-1,3-thiazol-2-amine；5-benzyl-4-phenyl-1,3-thiazol-2-amine
• CAS: 905592-30-5
• 化学式: C₁₆H₁₄N₂S
• 分子量: 266.367
• InChiKey: OJQAMANXTFAFPE-UHFFFAOYSA-N

物化性质

• 沸点：
  474.0±24.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  67.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-benzyl-4-phenylthiazol-2-amine 在 sodium tetrahydroborate 、 对甲苯磺酸 作用下， 以 乙醇 、 甲苯 为溶剂， 生成 5-benzyl-N-(4-methoxybenzyl)-4-phenylthiazol-2-amine
  参考文献：
  名称：

  2,4,5-Trisubstituted thiazole derivatives: A novel and potent class of non-nucleoside inhibitors of wild type and mutant HIV-1 reverse transcriptase

  摘要：

  Novel 2,4,5-trisubstituted thiazole derivatives (TSTs) were designed and synthesized as HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs). Among the thirty-eight synthesized target compounds, thirty TSTs showed potent inhibition against HIV-1 replication in wild type HIV-1 at submicromolar concentrations (from 0.046 to 9.59 mu M). Compounds 21, 23 and 24 were also tested on seven NNRTI-resistant HIV-1 strains, and all exhibited inhibitory effects with fold changes in IC50 ranging from 2.6 to 111, which were better than those of nevirapine (15.6-fold-371-fold). Docking simulations of compound 24 revealed a reasonable mechanism for the binding mode, and three-dimensional quantitative structure activity relationship (3-DQSAR) studies on this novel series of TST further elucidated the structure-activity relationship (SAR). The results suggested the great potential of TSTs as a novel class of NNRTIs with antiviral efficacy and a good resistance profile. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.07.072
• 作为产物：
  描述：

  ω-苄基苯乙酮 在 copper(ll) bromide 作用下， 以 乙醇 、 氯仿 、 乙酸乙酯 为溶剂， 反应 4.0h， 生成 5-benzyl-4-phenylthiazol-2-amine
  参考文献：
  名称：

  的发现ñ - （4-芳基-5-芳氧基-噻唑-2-基） -酰胺作为有效RORγt反向激动剂

  摘要：

  发现了一系列新颖的N-（4-芳基-5-芳氧基-噻唑-2-基）-酰胺作为RORγt反向激动剂。RORγtLBD中共晶体结构揭示的RORγt部分激动剂（2c）的结合模式分析表明，反向激动剂不会直接干扰H12与RORγtLBD之间的相互作用。详细的SAR探索导致鉴定出有效的RORγt反向激动剂，例如3m，pIC 50为8.0。该系列中的选定化合物在Th17细胞分化试验中显示出合理的活性，并且在小鼠肝微粒体中的固有清除率较低。

  DOI：

  10.1016/j.bmc.2015.07.068

文献信息

• [EN] CARBOXAMIDE OR SULFONAMIDE SUBSTITUTED THIAZOLES AND RELATED DERIVATIVES AS MODULATORS FOR THE ORPHAN NUCLEAR RECEPTOR ROR[GAMMA]<br/>[FR] THIAZOLES SUBSTITUÉS PAR CARBOXAMIDE OU SULFONAMIDE ET DÉRIVÉS APPARENTÉS EN TANT QUE MODULATEURS DU RÉCEPTEUR NUCLÉAIRE ORPHELIN ROR[GAMMA]
  申请人：PHENEX PHARMACEUTICALS AG

  公开号：WO2013178362A1

  公开（公告）日：2013-12-05

  The invention provides modulators for the orphan nuclear receptor RORy and methods for treating RORy mediated diseases by administering these novel RORy modulators to a human or a mammal in need thereof. Specifically, the present invention provides carboxamide or sulfonamide containing cyclic compounds of Formula (1), (1'), (100), (100'), (200) and (200') and the enantiomers, diastereomers, tautomers, /V-oxides, solvates and pharmaceutically acceptable salts thereof.

  这项发明提供了用于孤儿核受体RORγ的调节剂，以及通过向需要的人类或哺乳动物投与这些新型RORγ调节剂来治疗RORγ介导的疾病的方法。具体而言，本发明提供了含有环状化合物的羧酰胺或磺酰胺的化合物的公式（1）、（1'）、（100）、（100'）、（200）和（200'）及其对映体、二对映体、互变异构体、/V-氧化物、溶剂合物和药用可接受盐。
• [EN] COMPOUNDS USEFUL AS RETINOID-RELATED ORPHAN RECEPTOR GAMMA MODULATORS<br/>[FR] COMPOSÉS UTILES EN TANT QUE MODULATEURS DU RÉCEPTEUR APPARENTÉ AU RÉCEPTEUR DES RÉTINOÏDES GAMMA
  申请人：GLAXO GROUP LTD

  公开号：WO2012100734A1

  公开（公告）日：2012-08-02

  Disclosed are retinoid-related orphan receptor gamma (RORγ) modulators of Formula (I) and their use in the treatment of diseases mediated by RORγ, wherein the radicals have the meanings as defined in the invention.

  揭示了与视黄醇相关孤儿受体γ（RORγ）调节剂的化学式（I）及其在治疗由RORγ介导的疾病中的应用，其中基团具有发明中定义的含义。
• ORGANIC COMPOUNDS
  申请人：Forster Cornelia Jutta

  公开号：US20100022513A1

  公开（公告）日：2010-01-28

  The invention relates to compounds of formula (I): where A is an optionally substituted heteroaryl, useful for treating disorders mediated by acyl coA-diacylglycerol acyl transferase 1 (DGAT1), e.g. metabolic disorders. The invention also provides methods of treating such disorders, and compounds and compositions etc. for their treatment.

  该发明涉及式(I)的化合物： 其中A是可选择取代的杂环烷基，用于治疗由酰基辅酶A-二酰基甘油酰基转移酶1（DGAT1）介导的疾病，例如代谢性疾病。该发明还提供了治疗这种疾病的方法，以及用于治疗的化合物和组合物等。
• [EN] MODULATORS OF MYOCYTE LIPID ACCUMULATION AND INSULIN RESISTANCE AND METHODS OF USE THEREOF<br/>[FR] MODULATEURS D'ACCUMULATION DE LIPIDES DE MYOCYTES ET D'INSULINORÉSISTANCE ET LEURS PROCÉDÉS D'UTILISATION
  申请人：SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INST

  公开号：WO2017019772A1

  公开（公告）日：2017-02-02

  Formulations and methods for reducing blood glucose and/or increasing insulin signaling in a subject have been developed. The formulations include SBI-477 and compounds based on SBI-477 i.e., SBI-477 analogs (collectively, SBI-477 compounds) and/or Mondo family inhibitors, in an effective amount to inhibit intracellular lipid accumulation and/or increase cellular glucose uptake when compared to levels in a control subject not administered the composition. Also disclosed are methods of reducing intracellular lipid accumulation and/or increase glucose uptake in a subject in need thereof. The method includes administering to the subject an effective amount of SBI-477 compounds and/or Mondo family inhibitor to reducing intracellular lipid accumulation and/or increase glucose uptake in the subject. Also disclosed are method for treating one or more Myc-driven cancers, including neuroblastoma, lung squamous cell carcinoma/lung adenocarcinoma, liver hepatocellular carcinoma, colon adenocarcinoma, acute myeloid leukemia, and breast invasive carcinoma.

  已开发了用于降低血糖和/或增加受试者胰岛素信号的配方和方法。这些配方包括SBI-477和基于SBI-477的化合物，即SBI-477类似物（统称为SBI-477化合物）和/或Mondo家族抑制剂，以有效量抑制细胞内脂质积累和/或增加细胞葡萄糖摄取，与未施用该组合物的对照受试者相比。还公开了用于减少细胞内脂质积累和/或增加受试者葡萄糖摄取的方法。该方法包括向受试者施用足够量的SBI-477化合物和/或Mondo家族抑制剂，以减少受试者细胞内脂质积累和/或增加葡萄糖摄取。还公开了用于治疗一种或多种Myc驱动的癌症的方法，包括神经母细胞瘤、肺鳞状细胞癌/肺腺癌、肝细胞癌、结肠腺癌、急性髓系白血病和乳腺浸润性癌。
• Novel Acyl Coenzyme A: Diacylglycerol Acyltransferase 1 Inhibitors-Synthesis and Biological Activities of N-(Substituted heteroaryl)-4-(substituted phenyl)-4-oxobutanamides
  作者：Yoshihisa Nakada、Masaki Ogino、Kouhei Asano、Kazuko Aoki、Hiroshi Miki、Toshihiro Yamamoto、Koki Kato、Minori Masago、Norikazu Tamura、Mitsuyuki Shimada

  DOI：10.1248/cpb.58.673

  日期：——

  discover new small molecule diacylglycerol acyltransferase (DGAT)-1 inhibitors, screening of our in-house chemical library was carried out using recombinant human DGAT-1 enzyme. From this library, the lead compound 1a was identified as a new class of DGAT-1 inhibitor. A series of novel N-(substituted heteroaryl)-4-(substituted phenyl)-4-oxobutanamides 2 was designed from 1a, synthesized and evaluated

  在发现新的小分子二酰基甘油酰基转移酶（DGAT）-1抑制剂的程序中，使用重组人DGAT-1酶筛选了我们内部的化学文库。从该文库中，先导化合物1a被鉴定为一类新的DGAT-1抑制剂。从1a设计了一系列新型的N-（取代的杂芳基）-4-（取代的苯基）-4-氧代丁酰胺2，合成并评估了其对DGAT-1酶的抑制活性。在这些化合物中，发现N-（5-苄基-4-苯基-1,3-噻唑-2-基）-4-（4,5-二乙氧基-2-甲基苯基）-4-氧代丁酰胺9显示出有效的抑制作用。活性和良好的酶选择性。用3 mg / kg高脂饮食混合物在KKA（y）小鼠中施用4周后，有9只小鼠的体重增加和白色脂肪组织重量减少，而不会影响总食物摄入量。