1-phenyl-1H-benzo[d]imidazole-2-carbaldehyde | 6646-67-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 1-phenyl-1H-benzo[d]imidazole-2-carbaldehyde
• 英文别名: 2-Formyl-1-phenylbenzimidazol；N-phenyl-1H-benzimidazole-2-carboxaldehyde；1-phenyl-1H-benzoimidazole-2-carbaldehyde；1-phenylbenzimidazole-2-carboxaldehyde；1-phenylbenzimidazole-2-carbaldehyde
• CAS: 6646-67-9
• 化学式: C₁₄H₁₀N₂O
• 分子量: 222.246
• InChiKey: HJGHFDBOLBJAHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  四乙基(2-氧代-1,3-丙烷二基)二(膦酸酯) 、 1-phenyl-1H-benzo[d]imidazole-2-carbaldehyde 在 potassium carbonate 作用下， 以 乙醇 、 水 为溶剂， 以27%的产率得到(1E,4E)-1,5-bis(1-phenyl-1H-benzo[d]imidazol-2-yl)penta-1,4-dien-3-one
  参考文献：
  名称：

  Optimization of diarylpentadienones as chemotherapeutics for prostate cancer

  摘要：

  Our earlier studies indicate that (1E,4E)-1,5-bis(1-alkyl-1H-imidazol-2-yepenta-1,4-diene-3-ones and (1E,4E)-1,5-bis(1-alkyl-1H-benzo Mimidazol-2-yepenta-1,4-diene-3-ones exhibit up to 121-fold greater antiproliferative potency than curcumin in human prostate cancer cell models, but only 2-10 fold increase in mouse plasma concentrations. The present study aims to further optimize them as anti-prostate cancer agents with both good potency and bioavailability. (1E,4E)-1,5-Bis(1H-imidazol-2-yepenta-1,4-diene-3-one, the potential metabolic product of (1E,4E)-1,5-bis(1-alkyl-1H-imidazol-2-yepenta-1,4-diene-3-ones, was synthesized and evaluated for its anti-proliferative activity. The promising potency of 1,5-bis(1-alkyl-1H-imidazol-2-yepenta-1,4-diene-3-ones was completely abolished by removing the 1-alkyl group, suggesting the critical role of an appropriate group on the N1 position. We then envisioned that N-aryl substitution to exclude the C-H bond on the carbon adjacent to the N1 position (a-H) may increase the metabolic stability. Consequently, seven (1E,4E)-1,5-bis(1-aryl-1H-imidazol-2-yepenta-1,4-dien-3-ones and three (1E,4E)-1,5-bis(1-aryl-1H-benzo [d] imidazol-2-yOpenta-1,4-dien-3-ones, as well as three (1E,4E)-1,5-bis(1-aryl-1H-pyrrolo[3,2-b]pyridine-2-yepenta-1,4-dien-3-ones, were synthesized through a three-step transformation, including N-arylation via Ullmann condensation, formylation, and Horner-Wadsworth-Emmons reaction. Six optimal (1E,4E)-1,5-bis(1-aryl-1H-imidazol-2-yOpenta-1,4-dien-3-ones exhibit 24- to 375-fold improved potency as compared with curcumin. Replacement of the imidazole with bulkier benzoimidazole and 4-azaindole results in a substantial decrease in the potency. (1E,4E)-1,5-Bis(1-(2-methoxyphenyl)-1H-imidazol-2-yOpenta-1,4-dien-3-one (17d) was established as an optimal compound with both superior potency and good bioavailability that is sufficient to provide the therapeutic efficacy necessary to suppress in vivo tumor growth.

  DOI：

  10.1016/j.bmc.2018.08.018
• 作为产物：
  描述：

  2-甲基-1-苯基-1H-苯并咪唑 在 selenium(IV) oxide 作用下， 以 1,4-二氧六环 、 氯仿 、 乙酸乙酯 为溶剂， 生成 1-phenyl-1H-benzo[d]imidazole-2-carbaldehyde
  参考文献：
  名称：

  6-beta(substituted)-(S)-hydroxymethylpenicillanic acids and derivatives

  摘要：

  公式##STR1##的抗菌青霉素或其药用盐，其中R.sup.1是一个杂环基团，R是氢，具有对抗抗药性生物活性的某些羧基保护基团的残基或在体内容易水解的酯基团的残基。

  公开号：

  US04782050A1

文献信息

• Highly Enantioselective Synthesis of Chiral Benzhydrols via Manganese Catalyzed Asymmetric Hydrogenation of Unsymmetrical Benzophenones Using an Imidazole-Based Chiral PNN Tridentate Ligand
  作者：Fei Ling、Huacui Hou、Jiachen Chen、Sanfei Nian、Xiao Yi、Ze Wang、Dingguo Song、Weihui Zhong

  DOI：10.1021/acs.orglett.9b01056

  日期：2019.6.7

  A series of Mn(I) catalysts containing imidazole-based chiral PNN tridentate ligands with controllable “side arm” groups have been established, enabling the asymmetrical hydrogenation of unsymmetrical benzophenones with outstanding activity (up to 13 000 TON) and excellent enantioselectivity (up to >99% ee). This protocol uses K2CO3 as an industrially desirable base and features a wide substrate scope

  已经建立了一系列含有咪唑基手性PNN三齿配体和可控“侧臂”基团的Mn（I）催化剂，能够使不对称二苯甲酮进行不对称氢化，具有出色的活性（高达13000吨）和出色的对映选择性（高达> 99％ee）。该协议使用K 2 CO 3作为工业上可取的碱，并且具有广泛的底物范围和官能团耐受性。此外，催化剂中的亚胺基对于获得高活性和良好的对映选择性至关重要。
• Manganese‐Catalyzed Asymmetric Hydrogenation of Quinolines Enabled by π–π Interaction**
  作者：Chenguang Liu、Mingyang Wang、Shihan Liu、Yujie Wang、Yong Peng、Yu Lan、Qiang Liu

  DOI：10.1002/anie.202013540

  日期：2021.3

  The non‐noble metal‐catalyzed asymmetric hydrogenation of N‐heteroaromatics, quinolines, is reported. A new chiral pincer manganese catalyst showed outstanding catalytic activity in the asymmetric hydrogenation of quinolines, affording high yields and enantioselectivities (up to 97 % ee). A turnover number of 3840 was reached at a low catalyst loading (S/C=4000), which is competitive with the activity

  报道了非贵金属催化的N-杂芳族化合物喹啉的不对称氢化。一种新型手性钳式锰催化剂在喹啉的不对称氢化中表现出出色的催化活性，提供了高收率和对映选择性（高达97％ee）。在低催化剂负载量（S / C = 4000）下，达到了3840的周转率，与该反应中最有效的贵金属催化剂的活性相竞争。对映选择性的精确调节通过π-π相互作用来保证。
• Hidden signatures: new reagents for developing latent fingerprints
  作者：M. John Plater、Paul Barnes、Lauren K. McDonald、Sandy Wallace、Nia Archer、Thomas Gelbrich、Peter N. Horton、Michael B. Hursthouse

  DOI：10.1039/b820257e

  日期：——

  Aldehydes substituted with a quaternised pyridinium or quinolinium ring have been investigated for the development of latent fingerprints. Two routes were developed to a novel in situ formed azacyanine dye. This dye might form in the fingerprint where reagents are concentrated but does not form appreciably in solution experiments as evidenced by the lack of an absorption band at 600 nm. N-Alkyl and N-aryl

  已经研究了用季铵化吡啶鎓或喹啉鎓环取代的醛用于潜在指纹的形成。开发了两种途径以形成新颖的原位形成的杜鹃花青染料。这种染料可能会在浓缩试剂的指纹图中形成，但在溶液实验中不会明显形成，这是由于在600 nm处没有吸收带所证明的。N-烷基和N-芳基取代的苯并咪唑-2-甲醛具有稳定的荧光指纹。
• Manganese‐Catalyzed Asymmetric Hydrogenation of <i>3H</i> ‐Indoles
  作者：Chenguang Liu、Mingyang Wang、Yihan Xu、Yibiao Li、Qiang Liu

  DOI：10.1002/anie.202202814

  日期：2022.5.9

  General and efficient asymmetric hydrogenation (AH) of 3H-indoles has been realized using a well-defined chiral pincer manganese catalyst, with up to 99 % ee and a record TON of 72 350 in an earth-abundant metal-catalyzed AH reaction.

  使用定义明确的手性钳形锰催化剂实现了3H-吲哚的通用且有效的不对称氢化 (AH)，在地球资源丰富的金属催化 AH 反应中，ee 高达 99%，创纪录的 TON 为 72 350。
• CXCR4 CHEMOKINE RECEPTOR BINDING COMPOUNDS
  申请人：BRIDGER Gary J.

  公开号：US20080255197A1

  公开（公告）日：2008-10-16

  The present invention relates to compounds that bind to chemokine receptors, and having the formula wherein each A, X, Y, R 1 , R 2 and R 3 are substituents. The present invention also relates to methods of using such compounds, such as in treating HIV infection and inflammatory conditions such as rheumatoid arthritis. Furthermore, the present invention relates to methods to elevate progenitor and stem cell counts, as well as methods to elevate white blood cell counts, using such compounds.

  本发明涉及与趋化因子受体结合的化合物，其具有以下式子： 其中每个A、X、Y、R1、R2和R3均为取代基。本发明还涉及使用这种化合物的方法，例如用于治疗HIV感染和炎症性疾病，如类风湿性关节炎。此外，本发明还涉及使用这种化合物提高祖细胞和干细胞数量的方法，以及提高白细胞计数的方法。