CAS: 875781-44-5; 5-Bromo-3-Iodo-4,7-Diazaindole

该化合物是一种环环状有机化合物,其特点是有引信的火花和环,具有独特的化学特性;在2和7个位置分别存在溴和碘替代物,这增强了其反应能力和在各个领域的潜在应用,包括医药化学和材料科学;由于其结构特征,该产品可能表现出有趣的生物活动,使它成为进一步研究药物开发的试验对象;此外,卤素替代物能够影响其电子特性和溶解性,这对于其在化学反应和与生物目标互动方面的行为至关重要;作为丙烯-丙家族的成员,它也可能参与多种合成途径,允许产生更复杂的分子;总体而言,5H-丙烯[2,3-b] 丙烯,2-溴-7-iodo-是其在各个科学领域潜在应用的兴趣复合物.

英文名称5-Bromo-3-Iodo-4,7-Diazaindole
中文名称2-溴-7-碘-5H-吡咯并[2,3-b]吡嗪
IUPAC名称2-bromo-7-iodo-5H-pyrrolo[2,3-b]pyrazine
其它别名2-溴-7-碘-5H-吡咯并[3,2-B]吡嗪; 4H-Pyrrolo[2,3-B]Pyrazine,2-Bromo-7-Iodo- (9Ci)
CAS编号875781-44-5
MFCD编号:MFCD09878696
EINECS号:892-106-6
分子式:C6H3BrIN3分子量:323.919
产品CID: 1883696
产品分类有机原料→分子砌块→芳杂环类化合物→吡咯类化合物

相似结构搜索
InChIKey: ULGMTONBTOMHOK-UHFFFAOYSA-N
InChI=1S/C6H3BrIN3/c7-4-2-10-6-5(11-4)3(8)1-9-6/h1-2H,(H,9,10)
计算化学: 氢键受体数2.0氢键供体数1.0可旋转键数*

相似化合物

875781-45-6 875781-43-4 889447-20-5

MSDS等安全信息

GHS符号GHS07
危险类别急性毒性类别4(经口)
特定目标器官毒性 - 单次接触类别3
皮肤腐蚀/刺激类别2
严重眼刺激类别2A
警示词Warning
危险描述H302 |吞咽有害.
H335 |可能引起呼吸道刺激.
H315 |造成皮肤刺激.
H319 |造成严重眼刺激.
防范说明P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501
危险品标志Xi
安全声明H303+H313+H333

欧盟法规

C&L通报

上下游产品

5-溴-4,7-二氮杂吲哚 2-Bromo-5H-Pyrrolo[2,3-B]Pyrazine 875781-43-4

合成工艺路线路线简述

合成目标产物 2-Bromo-7-Iodo-5H-Pyrrolo[2,3-B]Pyrazine 主要起始原料 5-Bromo-4,7-Diazaindole
24241-18-7 + 1066-54-2 = 875781-44-5
反应条件:1.1 Reagents: Triethylamine Catalysts: Cuprous Iodide,Dichlorobis(Triphenylphosphine)Palladium Solvents: Tetrahydrofuran; 5 Min,Rt; Overnight,Rt2.1 Reagents: Potassium Tert-Butoxide Solvents: N-Methyl-2-Pyrrolidone; Rt; 3 H,80 °C3.1 Reagents: N-Iodosuccinimide Solvents: Acetone; Rt; 2 H,Rt
标题:Synthesis And Structure-Activity Relationships Of 3,5-Disubstituted-Pyrrolo[2,3-B]Pyridines As Inhibitors Of Adaptor-Associated Kinase 1 With Antiviral Activity
作者:Verdonck,Sven; Et Al
参考文献:Journal Of Medicinal Chemistry 日期:2019 卷标:62(12) 页码:5810-5831]

5049-61-6 = 875781-44-5
反应条件:1.1 Reagents: N-Bromosuccinimide Solvents: Dimethyl Sulfoxide; 45 Min,Rt; 3 H,Rt2.1 Reagents: Triethylamine Catalysts: Cuprous Iodide,Dichlorobis(Triphenylphosphine)Palladium Solvents: Tetrahydrofuran; 5 Min,Rt; Overnight,Rt3.1 Reagents: Potassium Tert-Butoxide Solvents: N-Methyl-2-Pyrrolidone; Rt; 3 H,80 °C4.1 Reagents: N-Iodosuccinimide Solvents: Acetone; Rt; 2 H,Rt
标题:Synthesis And Structure-Activity Relationships Of 3,5-Disubstituted-Pyrrolo[2,3-B]Pyridines As Inhibitors Of Adaptor-Associated Kinase 1 With Antiviral Activity
作者:Verdonck,Sven; Et Al
参考文献:Journal Of Medicinal Chemistry 日期:2019 卷标:62(12) 页码:5810-5831]

875781-41-2 = 875781-44-5
反应条件:1.1 Reagents: Potassium Tert-Butoxide Solvents: N-Methyl-2-Pyrrolidone; Rt; 3 H,80 °C2.1 Reagents: N-Iodosuccinimide Solvents: Acetone; Rt; 2 H,Rt
标题:Synthesis And Structure-Activity Relationships Of 3,5-Disubstituted-Pyrrolo[2,3-B]Pyridines As Inhibitors Of Adaptor-Associated Kinase 1 With Antiviral Activity
作者:Verdonck,Sven; Et Al
参考文献:Journal Of Medicinal Chemistry 日期:2019 卷标:62(12) 页码:5810-5831

📜5-溴-4,7-二氮杂吲哚置于碘,Potassium Hydroxide体系中,用 N,N-二甲基甲酰胺作为反应溶剂,化学反应 2.0H,以90%的收率获得产物2-溴-7-碘-5H-吡咯并[2,3-B]吡嗪
参考文献:Sph3127的发现:一种新型的,高效的,具有口服活性的直接肾素抑制剂
标题:Sph3127的发现:一种新型的,高效的,具有口服活性的直接肾素抑制剂
摘要:肾素是肾素-血管紧张素-醛固酮系统 (Raas) 中的限速酶,可调节血压和肾功能,因此是治疗高血压和心血管/肾脏疾病的有吸引力的靶标.然而,多年来,开发具有非常好口服生物利用度的直接肾素抑制剂 (Dri) 一直是一项长期挑战.这个问题被认为是因为大多数报道的 Dri 是肽样结构或非肽样结构,分子量 (Mw) > 600.因此,我们试图找到 Mw < 500 的非肽模拟 Dri,并发现有前景的2-氨基甲酰基吗啉衍生物4.在我们努力改善4在没有显着增加 Mw 的情况下,我们发现了化合物18 (Sph3127),它在临床前模型中表现出比阿利吉仑更高的生物利用度和更有效的抗高血压作用,并已完成原发性高血压的 Ii 期临床试验.
DOI:10.1021/acs.Jmedchem.2C00834

专利信息

专利号:US-9834551-B2
优先权日:2013-04-18
标题 :Substituted pyrrolo[2,3-b]pyrazines and substituted pyrazolo[3,4-b]pyridines as ITK and JAK kinase inhibitors
发明人：VANKAYALAPATI HARIPRASAD; YERRAMREDDY VENKATAKRISHNAREDDY; GANGIREDDY PARAMAREDDY; APPALANENI RAJENDRA P
权利人:ARRIEN PHARMACEUTICALS LLC
摘要:The present invention relates to compounds described by Formula I: n nsalts thereof, their synthesis, and their use as ITK and JAK3 inhibitors including such compounds and methods of using said compounds in the treatment of various diseases and or disorders such disease associated with abnormal cell growth such as autoimmune, inflammation, rheumatoid arthritis, systemic lupus erythematosus, atherosclerosis, ulcerative colitis, psoriatic arthritis, psoriasis, Crohn's, metabolic and cancer diseases. The present invention also provides pharmaceutically acceptable compositions comprising the compounds of the invention and methods of using the compositions and processes for preparing the compounds of the invention.

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合成参考文献

参考文献:10.1016/j.bmcl.2015.08.048
摘要:Burdick DJ, Wang S, Heise C, Pan B, Drummond J, Yin J, Goeser L, Magnuson S, Blaney J, Moffat J, Wang W, Chen H. Fragment-based discovery of potent ERK2 pyrrolopyrazine inhibitors. Bioorganic & Medicinal Chemistry Letters. 2015 Nov;25(21):4728–32. doi: 10.1016/j.bmcl.2015.08.048.