(2-(吡咯烷-1-基)嘧啶-5-基)硼酸 | 955374-13-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: (2-(吡咯烷-1-基)嘧啶-5-基)硼酸
• 英文名称: 2-(pyrrolidine-1-yl)pyrimidine-5-yl-boronic acid
• 英文别名: (2-(pyrrolidin-1-yl)pyrimidin-5-yl)boronic acid；2-(pyrrolidin-1-yl)pyrimidine-5-boronic acid；2-(1-pyrrolidinyl)pyrimidine-5-boronic acid；2-pyrrolidinopyrimidine-5-boronic acid；(2-pyrrolidin-1-ylpyrimidin-5-yl)boronic acid
• CAS: 955374-13-7
• 化学式: C₈H₁₂BN₃O₂
• mdl: MFCD10696938
• 分子量: 193.013
• InChiKey: SNAOVFKQOOJCHK-UHFFFAOYSA-N

物化性质

• 沸点：
  445.4±55.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.78
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  69.5
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  5-(3-bromo-4-methoxyphenyl)-3-(tert-butyl)-1-(2-hydroxyethyl)-6,7-dihydropyrazolo[4,3-e][1,4]diazepin-8(1H)-one 、 (2-(吡咯烷-1-基)嘧啶-5-基)硼酸 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3-Tert-butyl-1-(2-hydroxyethyl)-5-[4-methoxy-3-(2-pyrrolidin-1-ylpyrimidin-5-yl)phenyl]-6,7-dihydropyrazolo[4,3-e][1,4]diazepin-8-one
  参考文献：
  名称：

  Discovery of potent selective bioavailable phosphodiesterase 2 (PDE2) inhibitors active in an osteoarthritis pain model. Part II: Optimization studies and demonstration of in vivo efficacy

  摘要：

  Selective phosphodiesterase 2 (PDE2) inhibitors are shown to have efficacy in a rat model of osteoarthritis (OA) pain. We identified potent, selective PDE2 inhibitors by optimizing residual PDE2 activity in a series of phosphodiesterase 4 (PDE4) inhibitors, while minimizing PDE4 inhibitory activity. These newly designed PDE2 inhibitors bind to the PDE2 enzyme in a cGMP-like binding mode orthogonal to the cAMP-like binding mode found in PDE4. Extensive structure activity relationship studies ultimately led to identification of pyrazolodiazepinone, 22, which was >1000-fold selective for PDE2 over recombinant, full length PDEs 1B, 3A, 3B, 4A, 4B, 4C, 7A, 7B, 8A, 8B, 9, 10 and 11. Compound 22 also retained excellent PDE2 selectivity (241-fold to 419-fold) over the remaining recombinant, full length PDEs, 1A, 4D, 5, and 6. Compound 22 exhibited good pharmacokinetic properties and excellent oral bioavailability (F = 78%, rat). In an in vivo rat model of OA pain, compound 22 had significant analgesic activity 1 and 3 h after a single, 10 mg/kg, subcutaneous dose. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.082
• 作为产物：
  描述：

  四氢吡咯 、 2-氯嘧啶-5-硼酸 在 N,N-二异丙基乙胺 作用下， 以 N-甲基吡咯烷酮 为溶剂， 以70 %的产率得到(2-(吡咯烷-1-基)嘧啶-5-基)硼酸
  参考文献：
  名称：

  NOVEL COMPOUNDS FOR DIAGNOSIS

  摘要：

  The present invention relates to novel compounds of formula (I), or a detectably labelled compound, stereoisomer, racemic mixture, pharmaceutically acceptable salt, hydrate, or solvate thereof, that can be employed in the imaging of alpha-synuclein aggregates and determining an amount thereof. Furthermore, the compounds can be used for diagnosing a disease, disorder or abnormality associated with an alpha-synuclein aggregates (such as Parkinson's disease or such as multiple system atrophy (MSA)) determining a predisposition to such a disease, disorder or abnormality, prognosing such a disease, disorder or abnormality, monitoring the evolution of the disease in a patient suffering from such a disease, disorder or abnormality, monitoring the progression of such a disease, disorder or abnormality and predicting responsiveness of a patient suffering from such a disease, disorder or abnormality to a treatment thereof.

  公开号：

  WO2024126840A1

文献信息

• HETEROCYCLIC COMPOUNDS AS BIOGENIC AMINE TRANSPORT MODULATORS
  申请人：ANANTHAN Subramaniam

  公开号：US20160159809A1

  公开（公告）日：2016-06-09

  The present disclosure relates to certain amine derivatives of fused bicyclic heterocycles that inhibit the amine reuptake function of the biogenic amine transporters, dopamine transporter (DAT), serotonin transporter (SERT) and norepinephrine transporter (NET). Compounds of the present disclosure are potent inhibitors of the reuptake of dopamine (DA), serotonin (5-hydroxytryptamine, 5-HT) and norepinephrine (NE) with full or partial maximal efficacy. The compounds with partial maximal efficacy in inhibiting reuptake of all three biogenic amines are herein referred to as partial triple uptake inhibitors (PTRIs). Compounds of the present disclosure are useful for treating depression, pain and substance abuse and relapse to substance abuse and addiction to substances such as cocaine, methamphetamine, nicotine and alcohol. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

  本公开涉及融合的双环杂环胺衍生物，其抑制生物胺转运体的胺重摄取功能，包括多巴胺转运体（DAT）、血清素转运体（SERT）和去甲肾上腺素转运体（NET）。本公开的化合物是多巴胺（DA）、血清素（5-羟色胺，5-HT）和去甲肾上腺素（NE）重摄取的有效抑制剂，具有完全或部分的最大功效。部分三重重摄取抑制剂（PTRIs）指部分最大功效抑制三种生物胺的重摄取的化合物。本公开的化合物可用于治疗抑郁症、疼痛和物质滥用以及物质滥用和对可卡因、甲基安非他明、尼古丁和酒精等物质成瘾的复发。该摘要旨在作为特定领域搜索的扫描工具，不旨在限制本发明。
• Discovery of potent selective bioavailable phosphodiesterase 2 (PDE2) inhibitors active in an osteoarthritis pain model. Part II: Optimization studies and demonstration of in vivo efficacy
  作者：Mark S. Plummer、Joseph Cornicelli、Howard Roark、Donald J. Skalitzky、Charles J. Stankovic、Susan Bove、Jayvardhan Pandit、Annise Goodman、James Hicks、Aurash Shahripour、David Beidler、Xiao Kang Lu、Brian Sanchez、Christopher Whitehead、Ron Sarver、Timothy Braden、Richard Gowan、Xi Qiang Shen、Katherine Welch、Adam Ogden、Nalini Sadagopan、Heidi Baum、Howard Miller、Craig Banotai、Cindy Spessard、Sandra Lightle

  DOI：10.1016/j.bmcl.2013.03.082

  日期：2013.6

  Selective phosphodiesterase 2 (PDE2) inhibitors are shown to have efficacy in a rat model of osteoarthritis (OA) pain. We identified potent, selective PDE2 inhibitors by optimizing residual PDE2 activity in a series of phosphodiesterase 4 (PDE4) inhibitors, while minimizing PDE4 inhibitory activity. These newly designed PDE2 inhibitors bind to the PDE2 enzyme in a cGMP-like binding mode orthogonal to the cAMP-like binding mode found in PDE4. Extensive structure activity relationship studies ultimately led to identification of pyrazolodiazepinone, 22, which was >1000-fold selective for PDE2 over recombinant, full length PDEs 1B, 3A, 3B, 4A, 4B, 4C, 7A, 7B, 8A, 8B, 9, 10 and 11. Compound 22 also retained excellent PDE2 selectivity (241-fold to 419-fold) over the remaining recombinant, full length PDEs, 1A, 4D, 5, and 6. Compound 22 exhibited good pharmacokinetic properties and excellent oral bioavailability (F = 78%, rat). In an in vivo rat model of OA pain, compound 22 had significant analgesic activity 1 and 3 h after a single, 10 mg/kg, subcutaneous dose. (C) 2013 Elsevier Ltd. All rights reserved.
• NOVEL COMPOUNDS FOR DIAGNOSIS
  申请人：[en]AC IMMUNE SA

  公开号：WO2024126840A1

  公开（公告）日：2024-06-20

  The present invention relates to novel compounds of formula (I), or a detectably labelled compound, stereoisomer, racemic mixture, pharmaceutically acceptable salt, hydrate, or solvate thereof, that can be employed in the imaging of alpha-synuclein aggregates and determining an amount thereof. Furthermore, the compounds can be used for diagnosing a disease, disorder or abnormality associated with an alpha-synuclein aggregates (such as Parkinson's disease or such as multiple system atrophy (MSA)) determining a predisposition to such a disease, disorder or abnormality, prognosing such a disease, disorder or abnormality, monitoring the evolution of the disease in a patient suffering from such a disease, disorder or abnormality, monitoring the progression of such a disease, disorder or abnormality and predicting responsiveness of a patient suffering from such a disease, disorder or abnormality to a treatment thereof.