4-苯基-3,6-二氢-2H-吡啶-1-羧酸叔丁酯 | 186347-72-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 4-苯基-3,6-二氢-2H-吡啶-1-羧酸叔丁酯
• 英文名称: tert-butyl 4-phenyl-3,6-dihydro-2H-pyridine-1-carboxylate
• 英文别名: Tert-butyl 4-phenyl-5,6-dihydropyridine-1(2H)-carboxylate
• CAS: 186347-72-8
• 化学式: C₁₆H₂₁NO₂
• mdl: MFCD11977149
• 分子量: 259.348
• InChiKey: OESDBFQMFCAJFP-UHFFFAOYSA-N

物化性质

• 沸点：
  362.4±42.0 °C(Predicted)
• 密度：
  1.079±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.437
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  4-苯基-3,6-二氢-2H-吡啶-1-羧酸叔丁酯 在 palladium on activated charcoal 、 氢气 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 4-苯基哌啶
  参考文献：
  名称：

  Synthesis and biological evaluation of 1-(isoxazol-5-ylmethylaminoethyl)-4-phenyl tetrahydropyridine and piperidine derivatives as potent T-type calcium channel blockers with antinociceptive effect in a neuropathic pain model

  摘要：

  New tetrahydropyridinyl and piperidinyl ethylamine derivatives were designed with hypothetical mapping on pharmacophore model generated from ligand-based virtual screening. The designed compounds were synthesized, and their inhibitory activities on T-type calcium channel were assayed using FDSS and patch-clamp assay. Among them, compounds 7b and 10b showed potent T-type calcium current blocking activity against Ca(v)3.1 (alpha(1G)) and Ca(v)3.2 (alpha(1H)) channel simultaneously. With hERG and pharmacokinetics studies, compounds 7b and 10b were evaluated for the antinociceptive effect on rat model of neuropathic pain. They were significantly effective in decreasing the pain responses to mechanical and cold allodynia induced by spinal nerve ligation. These results suggest that modulation of alpha(1G) and am subtype T-type calcium channels may provide a promising approach for the treatment of neuropathic pain. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.12.056
• 作为产物：
  描述：

  4-羟基-4-苯基哌啶-1-羧酸叔丁酯 在 acid 作用下， 生成 4-苯基-3,6-二氢-2H-吡啶-1-羧酸叔丁酯
  参考文献：
  名称：

  化学修饰芳基-1,2,3,6-四氢吡啶并嘧啶衍生物以发现促肾上腺皮质激素释放因子（1）受体拮抗剂：芳基-1,2,3,6-四氢吡啶并嘌呤，-3H-1,2,3-三唑并[4,5-d]嘧啶，-嘌呤-8-和-7H-吡咯并[2,3-d]嘧啶衍生物。

  摘要：

  非肽CRF（1）拮抗剂的结构亲和关系（SAR）表明，此类拮抗剂可以由三个单元构成：疏水单元（上区域），质子接受单元（中央区域）和芳族单元（下降区域）。最近，已经报道了通过修饰中央区域获得的各种非肽促肾上腺皮质激素释放因子（1）（CRF（1））受体拮抗剂。相比之下，我们修改了Up-Area并提出了包含有效CRF受体配体1a-c的4-或5-芳基-1,2,3,6-四氢吡啶并嘧啶衍生物，并提出了4-或5-芳基-1， 2,3,6-四氢吡啶基部分可以用作向上区域中的取代基。我们的兴趣转向化学修饰，其中1a-c的嘧啶环被其他杂环取代，即2、3H-1,2,3-三唑并[4，3的5-d]嘧啶环，4的嘌呤-8-环和5的7H-吡咯并[2,3-d]嘧啶环。其中，5-芳基-1,2,3,6-四氢吡啶基嘌呤化合物6j（CRA0186）对CRF（1）受体的亲和力最高（IC（50）= 20nM）。我们在这里报告衍生物6-9的合成和SAR。

  DOI：

  10.1016/s0968-0896(01)00005-0

文献信息

• Benzoxazinyl-amidocyclopentyl-heterocyclic modulators of chemokine receptors
  申请人：Goble D. Stephen

  公开号：US20070238723A1

  公开（公告）日：2007-10-11

  Cyclopentyl compounds linked to a benzoxazinyl group through an amido moiety utilizing the ring nitrogen of the benzoxazine, and further substituted with a heterocyclic moiety, such compounds represented by formula I: which are used to modulate the CCR-2 chemokine receptor to prevent or treat inflammatory and immunoregulatory disorders and diseases, allergic diseases, atopic conditions including allergic rhinitis, dermatitis, conjunctivitis, and asthma, as well as autoimmune pathologies such as rheumatoid arthritis and atherosclerosis; and pharmaceutical compositions comprising these compounds and the use of these compounds and compositions.

  环戊基化合物通过酰胺基团与苯并噁唑基团相连，利用苯并噁唑环的环氮原子，并进一步用杂环基团取代，这些化合物由式I表示： 用于调节CCR-2趋化因子受体，以预防或治疗炎症和免疫调节性疾病和疾病，过敏性疾病，包括过敏性鼻炎，皮炎，结膜炎和哮喘，以及类风湿性关节炎和动脉粥样硬化等自身免疫病理病变；以及包含这些化合物的药物组合物和这些化合物和组合物的使用。
• COMPOUNDS AND USES THEREOF
  申请人：Yumanity Therapeutics, Inc.

  公开号：US20190330198A1

  公开（公告）日：2019-10-31

  The present invention features compounds useful in the treatment of neurological disorders. The compounds of the invention, alone or in combination with other pharmaceutically active agents, can be used for treating or preventing neurological disorders.

  本发明涉及用于治疗神经系统疾病的化合物。本发明的化合物可以单独或与其他药用活性剂结合使用，用于治疗或预防神经系统疾病。
• Synthesis of Functionalized Difluorocyclopropanes: Unique Building Blocks for Drug Discovery
  作者：Roman M. Bychek、Vadym V. Levterov、Iryna V. Sadkova、Andrey A. Tolmachev、Pavel K. Mykhailiuk

  DOI：10.1002/chem.201705708

  日期：2018.8.22

  Difluorocyclopropane‐containing building blocks for drug discovery were synthesized from the functionalized alkenes and TMSCF3/NaI. Novel fluorinated acids, amines, amino acids, alcohols, ketones and sulfonyl chlorides were obtained.

  由功能化烯烃和TMSCF 3 / NaI合成了用于药物发现的含二氟环丙烷的结构单元。获得了新颖的氟化酸，胺，氨基酸，醇，酮和磺酰氯。
• Highly Enantioselective Organocatalytic Oxidative Kinetic Resolution of Secondary Alcohols Using Chiral Alkoxyamines as Precatalysts: Catalyst Structure, Active Species, and Substrate Scope
  作者：Keiichi Murakami、Yusuke Sasano、Masaki Tomizawa、Masatoshi Shibuya、Eunsang Kwon、Yoshiharu Iwabuchi

  DOI：10.1021/ja509766f

  日期：2014.12.17

  The development and characterization of enantioselective organocatalytic oxidative kinetic resolution (OKR) of racemic secondary alcohols using chiral alkoxyamines as precatalysts are described. A number of chiral alkoxyamines have been synthesized, and their structure-enantioselectivity correlation study in OKR has led us to identify a promising precatalyst, namely, 7-benzyl-3-n-butyl-4-oxa-5-azahomoadamantane

  描述了使用手性烷氧基胺作为预催化剂的外消旋仲醇的对映选择性有机催化氧化动力学拆分 (OKR) 的开发和表征。已经合成了许多手性烷氧基胺，它们在 OKR 中的结构-对映选择性相关性研究使我们确定了一种有前途的前催化剂，即 7-苄基-3-正丁基-4-氧杂-5-氮杂高金刚烷，它提供了各种手性脂肪族仲醇（ee 高达 >99%，k(rel) 高达 296）。在一项机理研究中，含氯氧铵物种被确定为烷氧基胺预催化剂原位生成的活性物种，并且发现氯原子对于高反应性和对映选择性至关重要。
• Saturated Nitrogen and N-Acylated Heterocycles Potentiating the Activity of an Active Antibiotic against Mycobacteria
  申请人：UNIVERSITE DE DROIT ET DE LA SANTE DE LILLE 2

  公开号：US20150307471A1

  公开（公告）日：2015-10-29

  The present invention concerns a compound of general formula (I): in which n=0 or 1, R1 represents an optionally substituted alkyl chain, in particular substituted alkyl chain, in particular substituted with fluorine, X is chosen from N and CH, and R2 is chosen from optionally substituted phenyl and benzyl, wherein the heterocycles having 6 vertices comprise one, two or three nitrogen atoms. The present invention also concerns the use of this compound as a medicament, in particular in the treatment of bacterial and mycobacterial infections such as tuberculosis in combination with an antibiotic that is active against bacteria and/or mycobacteria, said compound potentiating the activity of said antibiotic.

  本发明涉及具有通用公式（I）的化合物：其中n=0或1，R1代表一个可选地取代的烷基链，特别是被取代的烷基链，尤其是用氟取代的，X选自N和CH，R2选自可选地取代的苯基和苄基，其中具有6个顶点的杂环包含一个、两个或三个氮原子。本发明还涉及将这种化合物用作药物，特别是在与对细菌和/或分枝杆菌有效的抗生素联合治疗细菌性和分枝杆菌性感染（如结核病）中的用途，所述化合物增强所述抗生素的活性。