[2-(4-bromo-phenyl)-4-methyl-thiazol-5-yl]-methanol | 61291-93-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: [2-(4-bromo-phenyl)-4-methyl-thiazol-5-yl]-methanol
• 英文别名: [4-methyl-2-(4-bromo-phenyl)thiazol-5-yl]-methanol；5-Thiazolemethanol, 2-(4-bromophenyl)-4-methyl-；[2-(4-bromophenyl)-4-methyl-1,3-thiazol-5-yl]methanol
• CAS: 61291-93-8
• 化学式: C₁₁H₁₀BrNOS
• 分子量: 284.176
• InChiKey: SHLFESLFEIDTFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  61.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [2-(4-bromo-phenyl)-4-methyl-thiazol-5-yl]-methanol 在 2-碘酰基苯甲酸 作用下， 以 二甲基亚砜 为溶剂， 生成 2-(4-bromo-phenyl)-4-methyl-thiazole-5-carbaldehyde
  参考文献：
  名称：

  Synthesis and antimycobacterial evaluation of new 5-(1-benzyl-1H-1,2,3-triazol-4-yl)-4-methyl-2-arylthiazole derivatives

  摘要：

  A new series of 5-(1-benzyl-1H-1,2,3-triazol-4-yl)-4-methyl-2-arylthiazole derivatives, 6a-w have been synthesized by click reaction of substituted benzylazide, 5a-d with 5-ethynyl-4-methyl-2-substituted phenylthiazole, 4a-f. The starting compounds 4-ethynyl-2-substituted phenylthiazole (4a-f) were synthesized from the corresponding thiazole aldehyde by using the Ohira-Bestmann reagent. The structure of the synthesized compounds was determined by spectral analysis. All the synthesized compounds were screened for their preliminary antitubercular activity against Mycobacterium tuberculosis H37Ra (MTB, ATCC 25177). Most of the synthesized compounds reported good activity against M. tuberculosis H37Ra strain with IC50 range of 0.58-8.23 mu g/mL. Compounds 6g and 6k reported good antitubercular activity with MIC90 values of 4.71 and 2.22 mu g/mL, respectively. Potential antimycobacterial activity suggested that these compounds could serve as good lead compounds for further optimization and development of a newer antitubercular candidate.[GRAPHICS].

  DOI：

  10.1007/s00044-019-02310-y
• 作为产物：
  描述：

  对溴硫代苯甲酰胺 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 2.0h， 生成 [2-(4-bromo-phenyl)-4-methyl-thiazol-5-yl]-methanol
  参考文献：
  名称：

  作为癌细胞线粒体靶向抑制剂的新型噻唑衍生物的设计、合成和生物学评价

  摘要：

  线粒体是细胞维持必要代谢活动的关键能量生产来源。针对功能失调的线粒体特征一直是线粒体相关疾病研究的热点。对癌性线粒体代谢的研究是肿瘤治疗中持续关注的问题。在此，我们基于我们早期对线粒体靶向剂的研究，着手评估新型 TPP-噻唑衍生物家族的抗癌活性。具体而言，我们设计并合成了一系列 TPP-噻唑衍生物，并通过 MTT 测定显示大多数合成的化合物有效抑制了三种癌细胞系（HeLa、PC3 和 MCF-7）。在结构修改后，我们探索了 SAR 关系并确定了最有希望的化合物R13（IC50 of 5.52 μM) 用于进一步研究。同时，我们进行了 ATP 产生测定以评估所选化合物对 HeLa 细胞能量产生的抑制作用。结果显示测试化合物显着抑制癌细胞的ATP产生。总体而言，我们设计并合成了一系列对癌细胞具有显着细胞毒性并有效抑制线粒体能量产生的化合物。

  DOI：

  10.1016/j.bioorg.2021.105015

文献信息

• [EN] HETEROCYCLIC COMPOUNDS AS MODULATORS OF PEROXISOME PROLIFERATOR ACTIVATED RECEPTORS, USEFUL FOR THE TREATMENT AND/OR PREVENTION OF DISORDERS MODULATED BY A PPAR<br/>[FR] COMPOSES HETEROCYCLIQUES UTILISES COMME MODULATEURS DES RECEPTEURS ACTIVES PROLIFERATEURS DU PEROXYSOME (PPAR), UTILES DANS LE TRAITEMENT ET/OU LA PREVENTION DE TROUBLES MODULES PAR UN PPAR
  申请人：LILLY CO ELI

  公开号：WO2005051945A1

  公开（公告）日：2005-06-09

  The present invention is directed to a compound of formula (I), or a pharmaceutically acceptable salt, solvate, hydrate or stereoisomer thereof, which is useful in treating or preventing disorders mediated by a peroxisome proliferator activated receptor (PPAR) such as syndrome X, type II diabetes, hyperglycemia, hyperlipidemia, obesity, coagaulopathy, hypertension, arteriosclerosis, and other disorders related to syndrome X and cardiovascular diseases.

  本发明涉及一种式(I)的化合物，或其药学上可接受的盐、溶剂合物、水合物或立体异构体，该化合物在治疗或预防由过氧化物酶体增殖激活受体（PPAR）介导的疾病中具有用途，如X综合征、2型糖尿病、高血糖、高脂血症、肥胖、凝血障碍、高血压、动脉硬化以及与X综合征和心血管疾病相关的其他疾病。
• Indole derivatives as ppar modulators
  申请人：Conner Eugene Scott

  公开号：US20060166983A1

  公开（公告）日：2006-07-27

  The present invention is directed to a method of treatment by modulating a peroxisome proliferator activated receptor by employing a compound of Structural Formula (I). The variables in (I) are defined herein. Also included are compounds, methods of making compounds, and pharmaceutical compositions. The compounds of the present invention are believed to be effective in treating and preventing Syndrome X, Type II diabetes, hyperglycemia, hyperlipidemia, obesity, coagaulopathy, hypertension, atherosclerosis, and other disorders related to Syndrome X and cardiovascular diseases.

  本发明涉及一种通过使用结构式(I)的化合物调节过氧化物酶体增殖物激活受体进行治疗的方法。式(I)中的变量在此定义。还包括化合物、制备化合物的方法和制药组合物。本发明的化合物被认为对治疗和预防X综合症、2型糖尿病、高血糖、高脂血症、肥胖症、凝血障碍、高血压、动脉粥样硬化以及其他与X综合症和心血管疾病有关的疾病有效。
• Peroxisome proliferator activated receptor modulators
  申请人：Conner Eugene Scott

  公开号：US20060084663A1

  公开（公告）日：2006-04-20

  The present invention is directed to compounds represented by the following structural formula, and pharmaceutically acceptable salts thereof, Formula I: wherein: (a) R5 is selected from the group consisting of (C 1 -C 6 ) alkyl, (C 1 -C 6 ) alkenyl, substituted aryl(C 0 -C 4 )alkyl, substituted aryloxy(C 0 -C 4 )alkyl, substituted arylthio(C 0 -C 4 )alkyl, unsubstituted aryl(C 0 -C 4 )alkyl, unsubstituted aryloxy(C 0 -C 4 )alkyl, and unsubstituted arylthio(C 0 -C 4 )alkyl; (b) T1 is C or N; (c) Q is selected from the group consisting of O, a single bond, O(CH 2 ) q and C; (d) q is 1 or 2; (e) W is selected from the group consisting of O, S, (CH 2 ) r N(R20)(CH 2 ) k , NHSO 2 , C(O)N(R20)(CH 2 ) r , (CH 2 ) r N(R20)C(O), and SO 2 ; (f) X is C m H 2m ; (g) m is 0, 1 or 2; (h) A is an functional group selected from the group consisting of carboxyl, C1-C3 alkylnitrile, carboxamide, and (CH 2 ) n COOR19; and (i) R19 is selected from the group consisting of hydrogen, optionally substituted C1-C4alkyl and optionally substituted arylmethyl.

  本发明涉及以下结构式所表示的化合物及其药学上可接受的盐，式I：其中：(a) R5选自(C1-C6)烷基，(C1-C6)烯基，取代芳基(C0-C4)烷基，取代芳氧基(C0-C4)烷基，取代芳硫基(C0-C4)烷基，未取代芳基(C0-C4)烷基，未取代芳氧基(C0-C4)烷基和未取代芳硫基(C0-C4)烷基组成的群体；(b) T1为C或N；(c) Q选自O，单键，O(CH2)q和C的群体；(d) q为1或2；(e) W选自O，S，(CH2)rN(R20)(CH2)k，NHSO2，C(O)N(R20)(CH2)r，(CH2)rN(R20)C(O)和SO2的群体；(f) X为CmH2m；(g) m为0，1或2；(h) A为从羧基，C1-C3烷基腈，羧酰胺和(CH2)nCOOR19的群体中选取的一个功能基团；(i) R19选自氢，可选取代的C1-C4烷基和可选取代的芳基甲基的群体。
• Fused heterocyclic derivates as ppar modulators
  申请人：Conner Eugene Scott

  公开号：US20060217374A1

  公开（公告）日：2006-09-28

  The present invention is directed to a method of treatment by modulating a peroxisome proliferator activated receptor by employing a compound of Structural Formula (I). The variables in I are defined herein. Also included are compounds, methods of making compounds, and pharmaceutical compositions. The compounds of the present invention are believed to be effective in treating and preventing Syndrome X, Type H diabetes, hyperglycemia, hyperlipidemia, obesity, coagaulopathy, hypertension, atherosclerosis, and other disorders related to Syndrome X and cardiovascular diseases.

  本发明涉及一种通过利用结构式（I）的化合物来调节过氧化物酶体增殖物激活受体进行治疗的方法。I中的变量在此定义。还包括化合物、制备化合物的方法和制药组合物。本发明的化合物被认为在治疗和预防综合征X、H型糖尿病、高血糖、高脂血症、肥胖症、凝血障碍、高血压、动脉粥样硬化和其他与综合征X和心血管疾病相关的疾病方面具有疗效。
• Heterocyclic Compounds As Modulators Of Peroxisome Proliferator Activated Receptors, Useful For The Treatment And/Or Prevention Of Disorders Modulated By A Ppar
  申请人：Henry James Robert

  公开号：US20080207685A1

  公开（公告）日：2008-08-28

  The present invention is directed to a compound of formula (I), or a pharmaceutically acceptable salt, solvate, hydrate or stereoisomer thereof, which is useful in treating or preventing disorders mediated by a peroxisome proliferator activated receptor (PPAR) such as syndrome X, type II diabetes, hyperglycemia, hyperlipidemia, obesity, coagaulopathy, hypertension, arteriosclerosis, and other disorders related to syndrome X and cardiovascular diseases.

  本发明涉及一种式为(I)的化合物，或其药学上可接受的盐、溶剂合物、水合物或立体异构体，该化合物用于治疗或预防由过氧化物酶体增殖激活受体（PPAR）介导的疾病，如X综合征、2型糖尿病、高血糖、高脂血症、肥胖症、凝血障碍、高血压、动脉硬化以及其他与X综合征和心血管疾病相关的疾病。