2-(3-丙氧基苯基)-1-乙胺 | 103686-13-1

• 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: 2-(3-丙氧基苯基)-1-乙胺
• 英文名称: 2-(3-propyloxyphenyl)ethylamine
• 英文别名: 2-(3-Propoxyphenyl)ethanamine
• CAS: 103686-13-1
• 化学式: C₁₁H₁₇NO
• mdl: MFCD08449852
• 分子量: 179.262
• InChiKey: CDJFWESZVLIVIS-UHFFFAOYSA-N

物化性质

• 沸点：
  281.7±15.0 °C(Predicted)
• 密度：
  0.979±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.454
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(3-丙氧基苯基)-1-乙胺 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 7.0h， 生成 4-(6-propoxy-3,4-dihydroisoquinolin-1-yl)benzenesulfonamide
  参考文献：
  名称：

  Synthesis, Structure–Activity Relationship Studies, and X-ray Crystallographic Analysis of Arylsulfonamides as Potent Carbonic Anhydrase Inhibitors

  摘要：

  A series of arylsulfonamides has been synthesized and investigated for the inhibition of some selected human carbonic anhydrase isoforms. The studied compounds showed significant inhibitory effects in the nanomolar range toward druggable isoforms (hCA VII, hCA IX, and hCA XIV) (K-i values from 4.8 to 61.7 nM), whereas they generally exhibited significant selectivity over hCA I and hCA II, that are ubiquitous and considered off-target isoforms. On the basis of biochemical data, we herein discussed structure-affinity relationships for this series of arylsulfonamides, suggesting a key role for alkoxy substituents in CA inhibition. Furthermore, X-ray crystal structures of complexes of two active inhibitors (1 and 2a) with hCA II allowed us to elucidate the main interactions between the inhibitor and specific amino acid residues within the catalytic site.

  DOI：

  10.1021/jm300112w
• 作为产物：
  描述：

  Benzene, 1-(2-nitroethenyl)-3-propoxy- 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 2-(3-丙氧基苯基)-1-乙胺
  参考文献：
  名称：

  苯乙基噻唑硫脲（PETT）化合物，一类新的HIV-1逆转录酶抑制剂。1. PETT类似物的合成及其基本的构效关系研究。

  摘要：

  描述了一系列新的有效的特异性HIV-1抑制化合物。该系列中的主要化合物N-（2-苯乙基）-N'-（2-噻唑基）硫脲（1）使用rCdG作为模板抑制HIV-1 RT，IC50为0.9 microM。在MT-4细胞中，化合物1抑制HIV-1的ED50为1.3 microM。细胞培养物中50％的细胞毒性剂量> 380 microM。通过将铅化合物概念上划分为四个象限来建立化学结构-活性关系（SAR）。搜救战略分为两个阶段。第一阶段涉及通过象限1-4的独立变化来优化抗病毒活性。第二阶段涉及制备结合了这些取代基中最好的杂化结构。进一步的SAR研究和药代动力学考虑导致鉴定N-（2-吡啶基）-N' -（5-溴-2-吡啶基）-硫脲（62; LY300046.HCl）可作为临床评估的候选药物。LY300046.HCl抑制HIV-1 RT的IC50为15 nM，在细胞培养中的ED50为20 nM。

  DOI：

  10.1021/jm00025a010

文献信息

• New Umami Amides: Structure–Taste Relationship Studies of Cinnamic Acid Derived Amides and the Natural Occurrence of an Intense Umami Amide in <i>Zanthoxylum piperitum</i>
  作者：Eric Frerot、Nathalie Neirynck、Isabelle Cayeux、Yoyo Hui-Juan Yuan、Yong-Ming Yuan

  DOI：10.1021/acs.jafc.5b02359

  日期：2015.8.19

  A series of aromatic amides were synthesized from various acids and amines selected from naturally occurring structural frameworks. These synthetic amides were evaluated for umami taste in comparison with monosodium glutamate. The effect of the substitution pattern of both the acid and the amine parts on umami taste was investigated. The only intensely umami-tasting amides were those made from 3,4-dimethoxycinnamic

  由选自天然结构框架的各种酸和胺合成了一系列芳族酰胺。与谷氨酸钠相比，评估了这些合成酰胺的鲜味。研究了酸和胺部分的取代方式对鲜味的影响。唯一强烈的鲜味酰胺是由3,4-二甲氧基肉桂酸制成的酰胺。胺部分对结构变化更耐受。带有烷基或烷氧基取代的苯乙胺残基的酰胺在水中以20 ppm的溶液显示出纯净的鲜味。随后使用超高效液相色谱仪和高四极杆Orbitrap质谱仪（UPLC / MS）来显示这些酰胺的天然存在。（E）-3-（3,4-二甲氧基苯基）-N-（4-甲氧基苯乙基）丙烯酰胺显示在花椒科的根和茎中，该花科是在韩国，日本和中国生长的芸香科植物。
• Probing Molecular Interactions between Human Carbonic Anhydrases (hCAs) and a Novel Class of Benzenesulfonamides
  作者：Elvira Bruno、Maria Rosa Buemi、Anna Di Fiore、Laura De Luca、Stefania Ferro、Andrea Angeli、Roberto Cirilli、Daniele Sadutto、Vincenzo Alterio、Simona Maria Monti、Claudiu T. Supuran、Giuseppina De Simone、Rosaria Gitto

  DOI：10.1021/acs.jmedchem.7b00264

  日期：2017.5.25

  isoforms. By enantioselective HPLC, we solved the racemic mixture and ascertained that the two enantiomers (30a and 30b) are equiactive inhibitors for hCA VII. Crystallographic and docking studies revealed the main interactions of these inhibitors into the carbonic anhydrase (CA) catalytic site, thus highlighting the relevant role of nonpolar contacts for this class of hCA inhibitors.

  根据hCA II与4-（3,4-二氢-1 H-异喹啉-2-羰基）苯磺酰胺（3）（PDB代码4Z1J）的复合物的X射线晶体学研究，4-设计了（1-芳基-3,4-二氢-1 H-异喹啉-2-羰基）苯磺酰胺（23 – 33）。具体而言，我们的想法是通过引入其他疏水/亲水功能来提高对可药物异构体的选择性。在合成和测试的化合物中，（R，S）-4-（6,7-二羟基-1-苯基-3,4-四氢异喹啉-1 H -2-羰基）苯磺酰胺（30）对大脑表达的hCA VII（K i = 0.20 nM ）表现出显着的抑制作用，并且对更广泛分布的hCA I和hCA II同工型具有选择性。通过对映选择性HPLC，我们解析了外消旋混合物，并确定了两种对映异构体（30a和30b）是hCA VII的等活性抑制剂。晶体学和对接研究揭示了这些抑制剂与碳酸酐酶（CA）催化位点之间的主要相互作用，从而突显了非极性接触对于此类hCA抑制剂的相关作用。
• Nitrogen containing heterocyclic compounds
  申请人：Burroughs Wellcome Co.

  公开号：US04968698A1

  公开（公告）日：1990-11-06

  Compounds of the formula (III): ##STR1## or salts or acyl derivatives thereof, for use as antifungal and antiprotozoal agents are disclosed. Compositions containing the compounds are also disclosed as are method for the preparation of the compounds and intermediates in their preparation.

  公式（III）的化合物：##STR1## 或其盐或酰基衍生物，用作抗真菌和抗原虫剂。还公开了含有该化合物的组合物，以及制备该化合物和其制备中间体的方法。
• N-substituted oligomers and methods for their synthesis, e.g. polyglycine bearing nucleic acid bases
  申请人：CHIRON CORPORATION

  公开号：EP1258492A1

  公开（公告）日：2002-11-20

  Poly N-substituted Glycines (poly NSGs), wherein the substituents bear purine or pyrimidine bases (R9) every second glycine: In addition, a solid phase method for the synthesis of N-substituted oligomers of more general structures is disclosed.The poly NSGs obtainable by this method can have a wide variety of side-chain substituents. Each N-substituted glycine monomer is assembled from two "sub-monomers" directly on the solid support. Each cycle of monomer addition consists of two steps: (1) acylation of a secondary amine bound to the support with an acylating agent comprising a leaving group capable of nucleophilic displacement by -NH2, such as a haloacetic acid, and (2) introduction of the side-chain by nucleophilic displacement of the leaving group, such as halogen (as a resin-bound α-haloacetamide) with a sufficient amount of a second sub-monomer comprising an -NH2 group, such as a primary amine, alkoxyamine, semicarbazide, acyl hydrazide, carbazate or the like. Repetition of the two step cycle of acylation and displacement gives the desired oligomers. The efficient synthesis of a wide variety of oligomeric NSGs using the automated synthesis technology of the present method makes these oligomers attractive candidates for the generation and rapid screening of diverse peptidomimetic libraries. The oligomers of the invention, such as N-substituted glycines (i.e. poly NSGs) disclosed here provide a new class of peptide-like compounds not found in nature, but which are synthetically accessible and have been shown to possess significant biological activity and proteolytic stability.

  聚 N-取代甘氨酸（poly NSGs），其中每第二个甘氨酸的取代基都带有嘌呤或嘧啶碱（R9）： 此外，还公开了一种用于合成更一般结构的 N-取代低聚物的固相方法。通过这种方法获得的聚 NSG 可以具有多种侧链取代基。每个 N-取代甘氨酸单体由两个 "子单体 "直接在固体支持物上组装而成。每个单体加成循环包括两个步骤：(1) 用包含能被 -NH2 亲核置换的离去基团（如卤乙酸）的酰化剂将与载体结合的仲胺酰化，以及 (2) 通过离去基团的亲核置换引入侧链、(2) 通过亲核置换离去基团，如卤素（作为与树脂结合的 α-卤代乙酰胺）和足量的包含 -NH2 基团的第二亚单体，如伯胺、烷氧基胺、半肼、酰肼、肼基脲或类似物，引入侧链。重复酰化和置换两步循环，即可得到所需的低聚物。利用本方法的自动合成技术可高效合成多种低聚 NSG，这使得这些低聚物在生成和快速筛选各种肽模拟库方面具有吸引力。本发明公开的低聚物，如 N-取代甘氨酸（即多 NSG），提供了一类新的肽类化合物，这类化合物在自然界中并不存在，但可以通过合成获得，而且已被证明具有显著的生物活性和蛋白水解稳定性。
• Taste modifying product
  申请人：Firmenich SA

  公开号：EP2912954A1

  公开（公告）日：2015-09-02

  The present invention relates to the use of a compound according to formula (I) in the form of any one of its stereoisomers or a mixture thereof, and wherein n is an integer from 0 to 2; the dotted line represents a carbon-carbon single or double bond; and each of R1 to R4, when taken independently from each other, represents a hydrogen atom or represents a R5 or OR5 group, R5 representing a C1 to C5, or even a C1 to C3, alkyl group; and optionally one of the groups R1 to R4 represents -OH; and/or when R1 and R2 are taken together, and/or R3 and R4 are taken together, represent a OCH2O group, provided said groups taken together are adjacent substituents of the phenyl group; as an ingredient to confer, enhance, improve or modify the kokumi or umami taste of a flavored article.

  本发明涉及一种符合式 (I) 的化合物的用途 以其任意一种立体异构体或其混合物的形式，其中 n 是 0 至 2 的整数； 虚线代表碳-碳单键或双键；当 R1 至 R4 各自独立存在时，代表氢原子或代表 R5 或 OR5 基团，R5 代表 C1 至 C5，甚至 C1 至 C3 烷基；R1 至 R4 基团中任选一个代表 -OH；和/或当 R1 和 R2 结合在一起时，和/或 R3 和 R4 结合在一起时，代表 OCH2O 基团，条件是上述结合在一起的基团是苯基的相邻取代基； 作为一种配料，赋予、增强、改善或改变调味品的 Kokumi 或鲜味。