4-nitro-5-styryl-1(3)H-imidazole | 69195-93-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-nitro-5-styryl-1(3)H-imidazole
• 英文别名: 4-nitro-5-trans-styryl-1(3)H-imidazole；4-Nitro-5-trans-styryl-1(3)H-imidazol；4-Nitro-5-(2-phenylethenyl)-1H-imidazole；5-nitro-4-[(E)-2-phenylethenyl]-1H-imidazole
• CAS: 69195-93-3
• 化学式: C₁₁H₉N₃O₂
• 分子量: 215.211
• InChiKey: QXGIKCKEMSLDCG-VOTSOKGWSA-N

物化性质

• 溶解度：
  1.8 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-nitro-5-styryl-1(3)H-imidazole 在 sodium hydroxide 、 potassium permanganate 作用下， 以 水 为溶剂， 反应 24.0h， 以80%的产率得到4-硝基-1H-咪唑-5-羧酸
  参考文献：
  名称：

  Hosmane, Ramachandra S.; Bhan, Anila, Journal of Heterocyclic Chemistry, 1990, vol. 27, # 7, p. 2189 - 2196

  摘要：

  DOI：
• 作为产物：
  描述：

  4-甲基-5-硝基咪唑 、 苯甲醛 以 various solvent(s) 为溶剂， 反应 21.0h， 以87%的产率得到4-nitro-5-styryl-1(3)H-imidazole
  参考文献：
  名称：

  Total synthesis of (8R)-3-(2-deoxy-.beta.-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol (pentostatin), the potent inhibitor of adenosine deaminase

  摘要：

  DOI：

  10.1021/jo00139a015

文献信息

• Studies related to the total synthesis of pentostatin. Approaches to the synthesis of (8<i>R</i>)-3,6,7,8-tetrahydroimidazo-[4,5-<i>d</i>][1,3]diazepin-8-ol and<i>N</i>-3 alkyl congeners
  作者：David C. Baker、Sterling R. Putt、H. D. Hollis Showalter

  DOI：10.1002/jhet.5570200324

  日期：1983.5

  A number of synthetic approaches to the (8R)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol ring system (3) of pentostatin (1) are reported. These involve the synthesis of a number of 4-C-derivatives of N-alkyl-5-amino- and 5-nitro-1H-imidazoles derived from 4-methyl-5-nitro-1H-imidazole.

  已报道了戊抑素（1）的（8 R）-3,6,7,8-四氢咪唑并[4,5- d ] [1,3]二氮杂-8-ol环系统（3）的许多合成方法。。这些涉及合成衍生自4-甲基-5-硝基-1 H-咪唑的N-烷基-5-氨基-和5-硝基-1 H-咪唑的多种4- C-衍生物。
• [EN] YAP1 INHIBITORS THAT TARGET THE INTERACTION OF YAP1 WITH OCT4<br/>[FR] INHIBITEURS DE YAP1 CIBLANT L'INTERACTION DE YAP1 AVEC OCT4
  申请人：H LEE MOFFITT CANCER CT & RES

  公开号：WO2018053446A1

  公开（公告）日：2018-03-22

  Binding of the transcriptional co-activator, YAP1, to the transcription factor Oct4, induces Sox2, which is a transcription actor necessary for the self-renewal of stem-like cells from non-small cell lung cancer. The WW domain of YAP1 binds to the PPxY motif of Oct4 to induce Sox2. Delivering a peptide corresponding to the WW domain could prevent the induction of Sox2 and stemness. Similarly, peptides and mimetics of the PPxY motif would be able to inhibit stemness. Disclosed are compounds that affect the Yap1:Oct4 interaction.

  转录共激活因子YAP1与转录因子Oct4的结合诱导Sox2，Sox2是非小细胞肺癌干细胞自我更新所必需的转录因子。YAP1的WW结构域与Oct4的PPxY基序结合以诱导Sox2。提供与WW结构域相对应的肽段可以阻止Sox2和干细胞特性的诱导。类似地，PPxY基序的肽段和模拟物能够抑制干细胞特性。揭示了影响Yap1:Oct4相互作用的化合物。
• PRODRUG FORMS OF KINASE INHIBITORS AND THEIR USE IN THERAPY
  申请人：Smaill Jeffrey Bruce

  公开号：US20120077811A1

  公开（公告）日：2012-03-29

  The invention provides novel prodrug compounds comprising a kinase inhibitor and a reductively-activated fragmenting aromatic nitroheterocycle or aromatic nitrocarbocycle trigger, where the compound carries a positive charge. In preferred embodiments, the compounds are of Formula I: where: X is any negatively charged counterion; R 1 is a group of the formula —(CH 2 ) n Tr, where Tr is an aromatic nitroheterocycle or aromatic nitrocarbocycle and —(CH 2 ) n Tr acts as a reductively-activated fragmenting trigger; and n is an integer from 0 to 6; R 2 , R 3 and R 4 may each independently be selected from aliphatic or aromatic groups of a tertiary amine kinase inhibitor (R 2 )(R 3 )(R 4 )N, or two of R 2 , R 3 , and R 4 may form an aliphatic or aromatic heterocyclic amine ring of a kinase inhibitor, or one of R 2 , R 3 and R 4 may be absent and two of R 2 , R 3 and R 4 form an aromatic heterocyclic amine ring of a kinase inhibitor. The compounds of the invention are useful in treating proliferative diseases such as cancer.

  本发明提供了新型的前药化合物，包括一种激酶抑制剂和一种还原活化的破裂芳香族硝基杂环或芳香族硝基碳杂环触发剂，其中该化合物带有正电荷。在优选实施例中，该化合物为式I：其中：X是任何带负电的反离子；R1是公式—(CH2)nTr的基团，其中Tr是芳香族硝基杂环或芳香族硝基碳杂环，—(CH2)nTr作为还原活化的破裂触发器；n是0到6的整数；R2、R3和R4可以各自独立地选择来自三级胺激酶抑制剂的脂肪族或芳香族基团(R2)(R3)(R4)N，或者R2、R3和R4中的两个可以形成激酶抑制剂的脂肪族或芳香族杂环胺环，或者R2、R3和R4中的一个可以缺失，R2、R3和R4中的两个可以形成激酶抑制剂的芳香族杂环胺环。该发明的化合物可用于治疗增殖性疾病，如癌症。
• YAP1 inhibitors that target the interaction of YAP1 with OCT4
  申请人：H. LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE, INC.

  公开号：US10906874B2

  公开（公告）日：2021-02-02

  Binding of the transcriptional co-activator, YAP1, to the transcription factor Oct4, induces Sox2, which is a transcription actor necessary for the self-renewal of stem-like cells from non-small cell lung cancer. The WW domain of YAP1 binds to the PPxY motif of Oct4 to induce Sox2. Delivering a peptide corresponding to the WAV domain could prevent the induction of Sox2 and stemness. Similarly, peptides and mimetics of the PPxY motif would be able to inhibit stemness. Disclosed are compounds that affect the Yap1:Oct4 interaction.

  转录共激活因子YAP1与转录因子Oct4结合可诱导Sox2，Sox2是非小细胞肺癌干样细胞自我更新所必需的转录因子。YAP1的WW结构域与Oct4的PPxY基序结合，诱导Sox2。输送与WAV结构域相对应的多肽可阻止Sox2的诱导和干性。同样，PPxY基团的多肽和模拟物也能抑制干性。已公开的化合物会影响Yap1与Oct4的相互作用。
• YAP1 inhibitors that target the interaction of YAP1 with Oct4
  申请人：H. LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE, INC.

  公开号：US11530182B2

  公开（公告）日：2022-12-20

  Binding of the transcriptional co-activator, YAP1, to the transcription factor Oct4, induces Sox2, which is a transcription actor necessary for the self-renewal of stem-like cells from non-small cell lung cancer. The WW domain of YAP1 binds to the PPxY motif of Oct4 to induce Sox2. Delivering a peptide corresponding to the WW domain could prevent the induction of Sox2 and stemness. Similarly, peptides and mimetics of the PPxY motif would be able to inhibit sternness. Disclosed are compounds that affect the Yap1:Oct4 interaction.

  转录共激活因子YAP1与转录因子Oct4结合可诱导Sox2，Sox2是非小细胞肺癌干样细胞自我更新所必需的转录因子。YAP1的WW结构域与Oct4的PPxY基序结合，诱导Sox2。输送与WW结构域相对应的多肽可以阻止Sox2的诱导和干性。同样，PPxY基团的多肽和模拟物也能抑制干性。已公开的化合物会影响 Yap1:Oct4 的相互作用。