CAS: 501951-42-4; (R)-1-(2-Bromophenyl)-3-(1-(5-(Trifluoromethyl)Pyridin-2-yl)Pyrrolidin-3-yl)Urea

该化合物是化学化学领域引起注意的一种化学化合物,特别是它作为诱杀酶磷酸酯4(PDE4). 这一抑制意义重大,因为PDE4参与对煽动性反应的管制,使SB-705498成为治疗各种发炎性疾病,包括哮喘和慢性阻塞性肺病(COPD)的潜在候选体.该化合物的特点是它与PDE4酶的具体结合性,有助于调节细胞内信号路径.就其化学结构而言,SB-705498是功能性团体的独特安排,有助于其生物活动和选择性.此外,它还因其药性皮肤特性进行了研究,包括吸收,分布,代谢和排泄物(ADME),这对于了解其治疗潜力和安全情况至关重要.

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上下游产品

N-[(3R)-1-[5-(三氟甲基)-2-吡啶基]-3-吡咯烷基]氨基甲酸叔丁酯 Tert-Butyl {(3R)-1-[5-(Trifluoromethyl)Pyridin-2-Yl]Pyrrolidin-3-Yl}Carbamate 717906-56-4
(R)-1-(5-Trifluoromethylpyridin-2-yl)Pyrrolidin-3-Ylamine 202267-15-0

合成工艺路线路线简述

    📜2-氯-5-三氟甲基吡啶置于盐酸,Potassium Carbonate体系中,用 1,4-二氧六环,乙醚,N,N-二甲基甲酰胺 作为反应溶剂,化学反应 9.0H,反应生成 Sb 705498; N-(2-溴苯基)-N'-[(3R)-1-[5-(三氟甲基)-2-吡啶基]-3-吡咯烷基]脲
    参考文献:Discovery Of Sb-705498: A Potent,Selective And Orally Bioavailable Trpv1 Antagonist Suitable For Clinical Development
    标题:Discovery Of Sb-705498: A Potent,Selective And Orally Bioavailable Trpv1 Antagonist Suitable For Clinical Development
    摘要:Small Molecule Antagonists Of The Vanilloid Receptor Trpv1 (Also Known As Vr1) Are Disclosed. Pyrrolidinyl Ureas Such As 8 And 15 (Sb-705498) Emerged As Lead Compounds Following Optimisation Of The Previously Described Urea Sb-452533. Pharmacological Studies Using Electrophysiological And Flipr-Ca2+-Based Assays Showed That Compounds Such As 8 And 15 Were Potent Antagonists Versus The Multiple Chemical And Physical Modes Of Trpv1 Activation (Namely Capsaicin,Acid And Noxious Heat). Furthermore,15 Possessed Suitable Developability Properties To Enable Progression Of This Compound Into In Vivo Studies And Subsequently Clinical Development. (C) 2006 Elsevier Ltd. All Rights Reserved.
    DOI:10.1016/j.Bmcl.2006.03.030

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    主要参考文献


    1: Bareille P, Murdoch RD, Denyer J, Bentley J, Smart K, Yarnall K, Zieglmayer P, Zieglmayer R, Lemell P, Horak F. The effects of a TRPV1 antagonist, SB-705498, in the treatment of seasonal allergic rhinitis. Int J Clin Pharmacol Ther. 2013 Jul;51(7):576-84. doi: 10.5414/CP201890. 77(5):777-88. doi: 10.1111/bcp.12219.
    3: Changani K, Hotee S, Campbell S, Pindoria K, Dinnewell L, Saklatvala P, Thompson SA, Coe D, Biggadike K, Vitulli G, Lines M, Busza A, Denyer J. Effect of the TRPV1 antagonist SB-705498 on the nasal parasympathetic reflex response in the ovalbumin sensitized guinea pig. Br J Pharmacol. 2013 Jun;169(3):580-9. doi: 10.1111/bph.12145.
    4: Gunthorpe MJ, Hannan SL, Smart D, Jerman JC, Arpino S, Smith GD, Brough S, Wright J, Egerton J, Lappin SC, Holland VA, Winborn K, Thompson M, Rami HK, Randall A, Davis JB. Characterization of SB-705498, a potent and selective vanilloid receptor-1 (VR1/TRPV1) antagonist that inhibits the capsaicin-, acid-, and heat-mediated activation of the receptor. J Pharmacol Exp Ther. 2007 Jun;321(3):1183-92. doi: 10.1124/jpet.106.116657. Epub 2007 Mar 28. 380(4):311-25. doi: 10.1007/s00210-009-0437-5. Epub 2009 Aug 19. 132(1-2):132-41. doi: 10.1016/j.pain.2007.06.006. Epub 2007 Jul 30. 16(12):3287-91. doi: 10.1016/j.bmcl.2006.03.030. Epub 2006 Mar 31. 52(4):267-76. doi: 10.5414/CP202013. 166(6):1822-32. doi: 10.1111/j.1476-5381.2012.01891.x.

    合成参考文献


    参考文献:10.1007/s00281-015-0528-y
    摘要:Yu X, Yu M, Liu Y, Yu S. TRP channel functions in the gastrointestinal tract. Semin Immunopathol. 2016 May;38(3):385–96. doi: 10.1007/s00281-015-0528-y.
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