R-1-苄基吡咯烷-2-甲醇 | 182076-49-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: R-1-苄基吡咯烷-2-甲醇
• 中文别名: N-苄基-D-脯氨醇；(R)-(+)-1-苄基吡咯烷-2-甲醇
• 英文名称: [(2R)-1-benzylpyrrolidin-2-yl]methanol
• 英文别名: (R)-1-benzyl-2-hydroxymethylpyrrolidine；(R)-1-benzyl-2-pyrrolidinemethanol；Bn-D-prolinol；(R)-(1-benzylpyrrolidin-2-yl)methanol
• CAS: 182076-49-9
• 化学式: C₁₂H₁₇NO
• mdl: MFCD00183619
• 分子量: 191.273
• InChiKey: ZAIQBJPTOXDDKA-GFCCVEGCSA-N

物化性质

• 沸点：
  313.3±0.0 °C(Predicted)
• 密度：
  1.082

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  R-1-苄基吡咯烷-2-甲醇 在 lithium aluminium tetrahydride 、 sodium azide 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 (S)-N-(1-benzyl-2-pyrrolidinylmethyl)-tert-butoxycarbamide
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of Naphthamides as Dopamine D₃ Receptor Ligands

  摘要：

  A series of naphthamides were synthesized, and the affinities of these compounds were determined for dopamine D-2 and D-3 receptors using radioligand binding techniques. The naphthamide compounds that were prepared include N-(1-alkylpiperidin-4-yl)-4-bromo-1-methoxy-2-naphthamides (1-6), (S)-N-(1-alkylpyrrolidin-3-yl)-4-bromo-1-methoxy-2-naphthamides (7-12), (R)-N-(1-alkylpyrrolidin-3-yl)-4-bromo-1-methoxy-2-naphthamides (13-18), (S)-N-(1-alkyl-2-pyrrolidinylmethyl)-4-bromo-1-methoxy-2-naphthamides (19 -25), (R)-N-(1-alkyl-2-pyrrolidinylmethyl)-4-bromo-1-methoxy-2-naphthamides (26-31), and N-(9-alkyl-9-azabicyclo-[3.3.1]nonan-3 beta -yl)-4- bromo-1-methoxy-2-naphthamides (32, 33). The results of in vitro radioligand binding studies indicated that the majority of the naphthamide analogues bound with high affinity at both the D-2 and D-3 dopamine receptor subtypes and most of the compounds demonstrated some selectivity for the dopamine D-3 dopamine receptor subtype. These results demonstrated that both the structure of the central amine moiety (piperidine, pyrrolidine, and 9-azabicyclo[3.3.1]nonane) ring and the N-(alkyl) substitution on the amine significantly effects the binding affinity at D-2 and D-3 dopamine receptors. The bulkiness of the N-(1-alkyl) substituent was found to (a) have no effect on pharmacologic selectivity, (b) increase the affinity at Ds receptors, or (c) decrease the affinity at D-2 receptors. The most potent analogue in this series was (S)-N-(1-cycloheptylpyrrolidin-3-yl)-4-bromo-1-methoxy-2-naphthamide (10), which had equilibrium dissociation (K-i) values of 1.8 and 0.2 nM for D-2 and D-3 receptors, respectively. The most selective analogue was (R)-N-(1-cycloheptyl-2-pyrrolidinylmethyl)-4-bromo-1-methoxy-2-naphthamide (30), which had K-i values of 62.8 and 2.4 nM for D-2 and D-3 receptors, respectively. Radioligand binding results for sigma receptors indicated that the structure of the amine moiety and the N-(l-alkyl) substitutions also significantly influence the affinity and selectivity of these compounds at the sigma (1) and sigma (2) sigma receptor subtypes. The two naphthamides containing a 9-azabicyclo[3.3.1]nonan-3 beta -yl central ring were found to be selective for sigma (2) receptors.

  DOI：

  10.1021/jm0100077
• 作为产物：
  描述：

  D-脯氨酸 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 64.0h， 生成 R-1-苄基吡咯烷-2-甲醇
  参考文献：
  名称：

  了解 3-氯哌啶的烷基化机制——核磁共振动力学研究和双环氮丙啶离子的分离

  摘要：

  在这项研究中，我们通过分离建议的中间体氮丙啶离子和 NMR 动力学研究来分析 3-氯哌啶的烷基化机理。这些预测中间体的双环结构通过单晶 XRD 得到证实，而动力学分析表明，gem 甲基化化合物与其相应的非甲基化类似物之间存在显着的反应性差异。

  DOI：

  10.1002/ejoc.202101072

文献信息

• PYRAZINECARBOXAMIDE COMPOUND
  申请人：ASTELLAS PHARMA INC.

  公开号：US20140323463A1

  公开（公告）日：2014-10-30

  [Problem] A compound which is useful as an inhibitor on EGFR T790M mutation kinase activity is provided. [Means for Solution] The present inventors have investigated a compound having an inhibitory action on an EGFR T790M mutation kinase, and have found that a pyrazinecarboxamide compound has an inhibitory action on an EGFR T790M mutation kinase, thereby completing the present invention. The pyrazinecarboxamide compound of the present invention has an inhibitory action on an EGFR T790M mutation kinase, and can be used as an agent for preventing and/or treating EGFR T790M mutation positive cancer, in another embodiment, EGFR T790M mutation positive lung cancer, in a still other embodiment, EGFR T790M mutation positive non-small cell lung cancer, in further still another embodiment, EGFR T790M mutation protein positive cancer, in further still another embodiment, EGFR T790M mutation protein positive lung cancer, in further still another embodiment, EGFR tyrosine kinase inhibitor-resistant cancer, in further still another embodiment, EGFR tyrosine kinase inhibitor-resistant lung cancer, and in further still another embodiment, EGFR tyrosine kinase inhibitor-resistant non-small cell lung cancer, or the like.

  提供一种作为EGFR T790M突变激酶活性抑制剂的化合物。 解决方案的手段 本发明人调查了一种对EGFR T790M突变激酶具有抑制作用的化合物，并发现吡嗪羧酰胺化合物对EGFR T790M突变激酶具有抑制作用，从而完成了本发明。本发明的吡嗪羧酰胺化合物对EGFR T790M突变激酶具有抑制作用，并可用作预防和/或治疗EGFR T790M突变阳性癌症的药剂，在另一实施例中，EGFR T790M突变阳性肺癌，在另一实施例中，EGFR T790M突变阳性非小细胞肺癌，在进一步的另一实施例中，EGFR T790M突变蛋白阳性癌症，在进一步的另一实施例中，EGFR T790M突变蛋白阳性肺癌，在进一步的另一实施例中，EGFR酪氨酸激酶抑制剂耐药癌症，在进一步的另一实施例中，EGFR酪氨酸激酶抑制剂耐药肺癌，在进一步的另一实施例中，EGFR酪氨酸激酶抑制剂耐药非小细胞肺癌等。
• Barbituric acid derivatives as inhibitors of TNF-alpha converting enzyme (TACE) and/or matrix metalloproteinases
  申请人：——

  公开号：US20030166647A1

  公开（公告）日：2003-09-04

  The present application describes novel barbituric acid derivatives of formula I: 1 or pharmaceutically acceptable salt or prodrug forms thereof, wherein A, B, L, R 1 , W, Z, U a , X a , Y a , and Z a are defined in the present specification, which are useful as TNF-&agr; converting enzyme (TACE) and matrix metalloproteinses (MMP) inhibitors.

  本申请描述了式I的新型巴比妥酸衍生物：1或其药用可接受的盐或前药形式，其中A、B、L、R1、W、Z、Ua、Xa、Ya和Za如本规范中定义，这些衍生物可用作TNF-α转化酶（TACE）和基质金属蛋白酶（MMP）抑制剂。
• Farnesyl protein transferase inhibitors
  申请人：——

  公开号：US20030040520A1

  公开（公告）日：2003-02-27

  Disclosed are compounds of the formula: 1 wherein R 8 represents a cyclic moiety to which is bound an imodazolylalkyl group; R 9 represents a carbamate, urea, amide or sulfonamide group; and the remaining substituents are as defined herein. Also disclosed is a method of treating cancer and a method of inhibiting famesyl protein transferase using the disclosed compounds.

  本发明涉及以下式子的化合物：1其中R8代表结合有一种咪唑基烷基的环状基团；R9代表氨基甲酸酯、尿素、酰胺或磺酰胺基团；其余取代基如本文中所定义。本发明还涉及使用上述化合物治疗癌症和抑制法美酰蛋白转移酶的方法。
• Penem derivatives and antimicrobial agent containing the same
  申请人：Ishiguro Masaji

  公开号：US20050004092A1

  公开（公告）日：2005-01-06

  A penem derivative represented by the following formula (I): wherein R 1 represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted alkenylthio group, a substituted or unsubstituted aralkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic thio group, a substituted or unsubstituted acylthio group, a mercapto group or a hydrogen atom, and R 2 represents a hydrogen atom or a carboxyl-protecting group; or a pharmacologically acceptable salt thereof. The compound (I) exhibits strong antibacterial activities, and especially, shows strong activities against MRSA. It is therefore useful not only as a general antibacterial agent but also as an antibacterial agent for MRSA against which no general antibacterial agents are recognized to be-effective.

  以下是公式（I）所代表的一种青霉烷衍生物： 其中，R1代表取代或未取代的烷基、取代或未取代的烯基、取代或未取代的芳基烷基、取代或未取代的芳基、取代或未取代的烷基硫基、取代或未取代的烯基硫基、取代或未取代的芳基烷基硫基、取代或未取代的芳基硫基、取代或未取代的杂环基、取代或未取代的杂环硫基、取代或未取代的酰基硫基、巯基或氢原子，R2代表氢原子或羧酸保护基；或其药学上可接受的盐。该化合物（I）表现出强大的抗菌活性，特别是对MRSA表现出强大的活性。因此，它不仅有用作一般抗菌剂，还有用作抗MRSA的抗菌剂，对于这种细菌，一般的抗菌剂被认为无效。
• Quinazolines and Their Use as Aurora Kinase Inhibitors
  申请人：Foote Kevin Michael

  公开号：US20080194556A1

  公开（公告）日：2008-08-14

  The invention provided a compound of formula (I) for use in the treatment of disease, in particular proliferative diseases such as cancer and for use in the preparation of medicaments for use in the treatment of proliferative diseases; the invention also processes for the preparation of such compounds, as well as pharmaceutical compositions containing them as active ingredient.

  该发明提供了一种式（I）的化合物，用于治疗疾病，特别是增生性疾病，如癌症，并用于制备治疗增生性疾病的药物；该发明还提供了制备这种化合物的方法，以及包含它们作为活性成分的药物组合物。