2-苯基-1H-咪唑-4,5-二甲酸 | 888-60-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-苯基-1H-咪唑-4,5-二甲酸
• 英文名称: 2-phenyl-1H-imidazole-4,5-dicarboxylic acid
• 英文别名: 2-phenylimidazole-4,5-dicarboxylic acid；2-phenyl-4,5-imidazoledicarboxylic acid
• CAS: 888-60-8
• 化学式: C₁₁H₈N₂O₄
• 分子量: 232.196
• InChiKey: GTYWKHXMYZVFSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  103
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 海关编码：
  2933290090

反应信息

• 作为反应物：
  描述：

  2-苯基-1H-咪唑-4,5-二甲酸 在 盐酸 、 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 592.0h， 生成 [1-methyl-5-(methylcarbamoyloxymethyl)-2-phenylimidazol-4-yl]methyl N-methylcarbamate
  参考文献：
  名称：

  Design, synthesis, antineoplastic activity, and chemical properties of bis(carbamate) derivatives of 4,5-bis(hydroxymethyl)imidazole

  摘要：

  A series of bis(carbamate) derivatives of 1,2-substituted 4,5-bis(hydroxymethyl)imidazoles were prepared and evaluated against murine P388 lymphocytic leukemia. Electron-withdrawing substituents at either N-1 or C-2 gave rise to inactive compounds. However, electron-donating substituents gave active compounds and the 2-(methylthio)-1-methyl derivative 2i (carmethizole), as the bis(N-methylcarbamate), was found to be very active. The derivative 2i, referred to by the name carmethizole, was also shown to be active against the MX-1 mammary xenograft, the human amelanotic melanoma cell line (LOX) xenograft, the M5076 sarcoma, and L1210 lymphocytic leukemia. The solution stability, water solubility, pKa, and log P of carmethizole are also reported.

  DOI：

  10.1021/jm00121a023
• 作为产物：
  描述：

  1,3-diazaazulene 在 potassium dichromate 、 sodium hydroxide 、 硫酸 作用下， 生成 2-苯基-1H-咪唑-4,5-二甲酸
  参考文献：
  名称：

  Benzoylation of 1,3-Diazaazulene

  摘要：

  DOI：

  10.1246/bcsj.32.841

文献信息

• [EN] PHENYL-ANILINE SUBSTITUTED BICYCLIC COMPOUNDS USEFUL AS KINASE INHIBITORS<br/>[FR] COMPOSES BICYCLIQUES A SUBSTITUTION PHENYL-ANILINE UTILISES COMME INHIBITEUR DE LA KINASE
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2005042537A1

  公开（公告）日：2005-05-12

  Compounds having the formula (I), and pharmaceutically acceptable salts, prodrugs, and solvates thereof, are useful as kinase inhibitors, wherein R, R1 , R2, R5, R6a, R6b, J, K, X and Z are as described in the specification.

  具有化学式（I）的化合物，以及其药学上可接受的盐、前药和溶剂化合物，可用作激酶抑制剂，其中R、R1、R2、R5、R6a、R6b、J、K、X和Z如规范中所述。
• Design and synthesis of optically active 2-phenylimidazolecarboxamides featuring amino acid motive
  作者：Roman Sivek、Oldřich Pytela、Filip Bureš

  DOI：10.1002/jhet.5570450611

  日期：2008.11

  sixteen new, optically active carboxamides 1-3 have been synthesized. These compounds based on the 2-phenylimidazole and featuring amino acid residues are linked on the 4-position by an amidic bond. Two general methods were used for their construction. Whereas the first method employs acylchlorides as a reactive species, the second one involves a condensation of mixed anhydrides with the amino acid counterparts

  总共合成了十六种新的旋光羧酰胺1-3。这些基于2-苯基咪唑并具有氨基酸残基的化合物通过酰胺键在4-位连接。使用两种通用方法进行构造。第一种方法采用酰氯作为反应性物质，而第二种方法则涉及混合酸酐与氨基酸对应物的缩合反应。实际上，第二种方法被证明比第一种方法更有效。初步将羧酰胺1-3作为N螯合配体进行了测试，并应用于亨利或阿尔多反应中，收率不佳或对映体过量。
• A 3D europium-organic-framework from phenyl imidazole dicarboxylate showing high sensitivity in detection of nitrobenzene
  作者：Q. Y. Huang、Y. Zhao、L. Fu、G. Li

  DOI：10.1134/s1070328417090032

  日期：2017.9

  luminescent MOF, namely, [Eu(µ3-HPhIDC)(µ2-C2O4)0.5(H2O)] · 2H2O} n (I) (H3PhIDC = 2-phenyl-1H-imidazole-4,5-dicarboxylic acid) has been hydrothermally synthesized and structurally characterized by single-crystal X-ray diffraction techniques (CIF file CCDC no. 1457365). The MOF I indicates characteristic sharp emission bands of Eu3+ ion, which is selectively sensitive to nitrobenzene- based derivatives

  一种基于Eu的发光MOF，即[Eu（µ 3 -HPhIDC）（µ 2 -C 2 O 4）0.5（H 2 O）]·2H 2 O} n（I）（H 3 PhIDC = 2-苯基-1 H-咪唑-4,5-二羧酸已被水热合成并通过单晶X射线衍射技术进行结构表征（CIF文件CCDC 1457365）。MOF I表示Eu 3+离子的特征性清晰发射带，该发射带对基于硝基苯的衍生物（硝基苯，2-硝基甲苯，3-硝基甲苯，1,3-二硝基苯和2,4-二硝基甲苯）选择性敏感。这些特性使 我是这些化学物质的潜在荧光传感器。
• [EN] PHARMACEUTICAL COMPOSITIONS AND COMBINATIONS COMPRISING INHIBITORS OF THE ANDROGEN RECEPTOR AND USES THEREOF<br/>[FR] COMPOSITIONS ET COMBINAISONS PHARMACEUTIQUES COMPRENANT DES INHIBITEURS DU RÉCEPTEUR DES ANDROGÈNES ET UTILISATIONS DE CELLES-CI
  申请人：ESSA PHARMA INC

  公开号：WO2020198712A1

  公开（公告）日：2020-10-01

  The present disclosure generally relates to pharmaceutical compositions and combinations comprising an androgen receptor N-terminal domain inhibitor or an inhibitor and a second therapeutically active agent, such as an CDK4/6 inhibitor, a Pin1 inhibitor (inhibitor of peptidyl-prolyl cis/trans isomerases), or an antiandrogen. In particular, the present disclosure relates to pharmaceutical compositions and combintaions useful for treatment of various cancers, for example breast cancer and prostate cancer. Further, the present disclosure relates administering an androgen receptor N-terminal domain inhibitor in combination with radiation therapy for treatment of various cancers.

  本公开涉及药物组合和制剂，包括雄激素受体N端域抑制剂或抑制剂和第二种治疗活性剂，例如CDK4/6抑制剂、Pin1抑制剂（肽前脯氨酸顺反异构酶抑制剂）或抗雄激素。特别地，本公开涉及用于治疗各种癌症的药物组合和制剂，例如乳腺癌和前列腺癌。此外，本公开还涉及将雄激素受体N端域抑制剂与放射治疗联合使用以治疗各种癌症。
• The photochemistry of α-Azidocinnamates - a reinvestigation
  作者：Otto Meth-Cohn、Nicola J.R Williams、Angus MacKinnon、Judith A.K Howard

  DOI：10.1016/s0040-4020(98)00537-7

  日期：1998.8

  efficient manner by photolysis using quartz equipment.1 We find that use of pyrex filters or ketone sensitisation instead of quartz leads to high yields of the presumed intermediate diastereomeric pair of aziridinoimidazoline dimers, as does brief irradiation in quartz. These dimers have been characterised by spectral and crystallographic methods, and shown to oxidise with DDQ to give imidazoledicarboxylic

  在其他地方已经报道了α-Azicdocinnamates通过使用石英设备进行光解以逐步有效的方式生成三聚体的一种非对映异构体。1我们发现，使用派热克斯滤光片或酮敏化代替石英会导致假定的中间非对映异构对叠氮基咪唑啉二聚体的高收率，就像在石英中短暂照射一样。这些二聚体已通过光谱和晶体学方法表征，并显示可与DDQ氧化生成咪唑二羧酸酯，而碱对两种二聚体非对映体的作用均导致一个重排的二聚体1，2-二氢嘧啶。令人惊讶地，只有两种非对映异构体二聚体的混合物才使三聚体进一步光解。