(R)-N-(1-(naphthalen-1-yl)ethyl)formamide | 15297-34-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-N-(1-(naphthalen-1-yl)ethyl)formamide
• 英文别名: N-[(1R)-1-(1-Naphthalenyl)ethyl]formamide；N-[(1R)-1-naphthalen-1-ylethyl]formamide
• CAS: 15297-34-4
• 化学式: C₁₃H₁₃NO
• 分子量: 199.252
• InChiKey: LBUNPZWRXVWADJ-SNVBAGLBSA-N

物化性质

• 沸点：
  420.7±24.0 °C(Predicted)
• 密度：
  1.108±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-N-(1-(naphthalen-1-yl)ethyl)formamide 在 盐酸 、 lithium aluminium tetrahydride 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醚 、 乙腈 为溶剂， 反应 5.75h， 生成 (R)-N-methyl-1-(naphthalen-1-yl)-N-(4-(trifluoromethoxy)benzyl)ethanamine hydrochloride
  参考文献：
  名称：

  Chiral N-benzyl-N-methyl-1-(naphthalen-1-yl)ethanamines and their in vitro antifungal activity against Cryptococcus neoformans, Trichophyton mentagrophytes and Trichophyton rubrum

  摘要：

  In the search for new antifungal compounds and to explore structure activity relationships, a series of 24 chiral benzyl amine type antifungals was synthesised and characterised. In vitro testing against the human pathogen Cryptococcus neoformans revealed that several derivatives had MIC50 values similar to that of the commercial drug Butenafine. All of these contained a bulky group in the para position of the benzyl fragment. Eighteen compounds were also tested for activity against the dermatophytes Trichophyton mentagrophytes and Trichophyton rubrum. Of these (R)-N-(4-tert-butylbenzyI)-N-methyl-1-(naphthalen-1-yl)ethanamine (MIC50,: 0.06 mu g/mL) and a para-benzyloxy substituted derivative (MIC50: 0.125 mu g/mL) possessed high activity. Testing of derivatives with a stereocentre at the benzylic carbon, revealed that (S)-stereochemistry was required for potency: a MIC50 value of 1 mu g/mL was obtained for (S)-1-(4-tert-butylphenyl)-N-methyl-N-(naphthalen-1-ylmethyl)ethanamine. Preparation of the corresponding fluoromethyl compound was achieved employing lipase B from Candida antarctica as catalyst in the key step. A low antifungal activity was observed for the fluorinated derivative indicating the importance of the amine basicity for the antifungal potency of these compounds. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.07.043
• 作为产物：
  描述：

  (R)-(-)-1-萘乙基异氰酸酯 在 二氯二茂锆 、 lithium tri-t-butoxyaluminum hydride 作用下， 以 四氢呋喃 、 2-甲基四氢呋喃 为溶剂， 反应 1.0h， 以92%的产率得到(R)-N-(1-(naphthalen-1-yl)ethyl)formamide
  参考文献：
  名称：

  化学选择性Schwartz试剂介导的异氰酸酯还原为甲酰胺

  摘要：

  在广泛可用的异氰酸酯中添加原位产生的Schwartz试剂构成了化学选择性，高产且通用的合成各种功能化甲酰胺的方法。立体和电子因素或敏感功能（酯，硝基，腈，烯烃）的存在不会影响该方法的潜力。观察到完全保留了起始材料中所含的立体化学信息。简要研究了甲酰胺在有机金属试剂亲核加成中的应用（Chida-Sato烯丙基化，Charette-Huang加到亚氨基三氟甲磺酸酯活化的酰胺中，硼酸酯的Matteson同源性）。

  DOI：

  10.1021/acs.orglett.6b01226

文献信息

• [EN] 3-HYDROXYPYRROLIDINE INHIBITORS OF 5'-METHYLTHIOADENOSINE PHOSPHORYLASE AND NUCLEOSIDASE<br/>[FR] INHIBITEURS 3-HYDROXYPYRROLIDINE DE 5'-MÉTHYLTHIOADÉNOSINE PHOSPHORYLASE ET NUCLÉOSIDASE
  申请人：ALBERT EINSTEIN COLLEGE OF YESHIVA UNIVERSITY

  公开号：WO2011008110A1

  公开（公告）日：2011-01-20

  The present invention relates to 3-hydroxypyrrolidine compounds of the general formula (I) which are inhibitors of 5'-methylthioadenosine phosphorylase or 5'-methylthioadenosine nucleosidase. The invention also relates to the use of these compounds in the treatment of diseases or conditions in which it is desirable to inhibit 5'-methylthioadenosine phosphorylase or 5'-methylthioadenosine nucleosidase including cancer, and to pharmaceutical compositions containing the compounds.

  本发明涉及一般式（I）的3-羟基吡咯烷化合物，这些化合物是5'-甲硫腺苷磷酸化酶或5'-甲硫腺苷核苷酸酶的抑制剂。该发明还涉及在治疗希望抑制5'-甲硫腺苷磷酸化酶或5'-甲硫腺苷核苷酶的疾病或症状中使用这些化合物，包括癌症，并且涉及含有这些化合物的药物组合物。
• Anti-Fertilization Activity of a Spirocyclic Sesquiterpene Isocyanide Isolated from the Marine Sponge<i>Geodia exigua</i>and Related Compounds
  作者：Emi OHTA、Mylene M. UY、Shinji OHTA、Mihoko YANAI、Toshifumi HIRATA、Susumu IKEGAMI

  DOI：10.1271/bbb.80071

  日期：2008.7.23

  (-)-10-epi-Axisonitrile-3, a spirocyclic sesquiterpene isocyanide obtained from the marine sponge Geodia exigua, immobilized sperm of sea urchin and starfish to block fertilization at the minimum effective concentration of 0.4 microg/ml. On the other hand, fertilized eggs developed normally to the gastrula stage in the presence of a 250-times higher concentration of the isocyanide. Analysis by (31)P

  （-）-10-epi-Axisonitrile-3，一种从海洋海绵Geodia exigua获得的螺环倍半萜异氰化物，以最小有效浓度0.4 microg / ml固定了海胆和海星的精子以阻止受精。另一方面，受精卵在异氰化物浓度高250倍的情况下正常发育至腹胚阶段。通过（31）P NMR进行的分析显示，经异氰化物处理的精子中存在磷酸肌酸的积累和无机磷酸盐的消耗，这表明（-）-10-epi-axisonitrile-3抑制了参与高能磷酸盐代谢的磷酸肌酸穿梭，从而固定精子以阻止受精。包含不同官能度的（-）-10-表轴腈-3或具有不同碳骨架的异氰酸酯的类似物均未显示出这种活性。
• Synthesis, Resolution, and Preliminary Evaluation of <i>trans</i>-2-Amino-6(5)-hydroxy-1-phenyl-2,3-dihydro-1<i>H</i>-indenes and Related Derivatives as Dopamine Receptors Ligands
  作者：Francesco Claudi、Gian Mario Cingolani、Antonio Di Stefano、Gianfabio Giorgioni、Francesco Amenta、Paolo Barili、Francesca Ferrari、Daniela Giuliani

  DOI：10.1021/jm960318v

  日期：1996.1.1

  optical resolution. The new compounds were evaluated for their affinity at the dopamine D1 and D2 receptors. The amines (+)- and (-)-14a, incorporating the D1 pharmacophore 2-phenyl-2-(3-hydroxyphenyl)ethylamine in a trans extended conformation, and their derivatives displayed D1 and D2 affinity in the nanomolar range. On the other hand, the enantiomers (+)- and (-)-14b, (+)- and (-)-15b displayed high

  本工作报告了反式-2-氨基-6-羟基-1-苯基-2,3-二氢-1H-茚[（+）-14a，（-）-14a]和反式- 2-氨基-5-羟基-1-苯基-2,3-二氢-1 H-茚[（+）-14b，（-）-14b]及其N，N-二正丙基[[+] -和（-）-15a，b]，N-甲基-N-烯丙基[（+）-和（-）-16a，b]和N-甲基-Nn-丙基[（+）和（-）- 17a，b]通过立体定向反应和光学拆分的组合获得的衍生物。评估了新化合物对多巴胺D1和D2受体的亲和力。胺（+）-和（-）-14a，以反式扩展构象结合D1药效团2-苯基-2-（3-羟苯基）乙胺，其衍生物在纳摩尔范围内显示D1和D2亲和力。另一方面，对映体（+）-和（-）-14b （+）-和（-）-15b对D1受体显示出高亲和力和选择性。在对大鼠（+）-14b以及在更大程度上（+）-15b的大鼠进行的初步行为研究中，它们促进了激烈的梳毛事件，因此
• 3-HYDROXYPYRROLIDINE INHIBITORS OF 5'-METHYLTHIOADENOSINE PHOSPHORYLASE AND NUCLEOSIDASE
  申请人：Evans Gary Brian

  公开号：US20120157479A1

  公开（公告）日：2012-06-21

  The present invention relates to 3-hydroxypyrrolidine compounds of the general formula (I) which are inhibitors of 5′-methylthioadenosine phosphorylase or 5′-methylthioadenosine nucleosidase. The invention also relates to the use of these compounds in the treatment of diseases or conditions in which it is desirable to inhibit 5′-methylthioadenosine phosphorylase or 5′-methylthioadenosine nucleosidase including cancer, and to pharmaceutical compositions containing the compounds.

  本发明涉及一般式(I)的3-羟基吡咯烷化合物，其为5'-甲基硫腺苷磷酸化酶或5'-甲基硫腺苷核苷酸酶的抑制剂。本发明还涉及使用这些化合物治疗需要抑制5'-甲基硫腺苷磷酸化酶或5'-甲基硫腺苷核苷酸酶的疾病或情况，包括癌症，并涉及含有这些化合物的药物组合物。
• Chiral additive induced self-disproportionation of enantiomers under MPLC conditions: preparation of enantiomerically pure samples of 1-(aryl)ethylamines from racemates
  作者：Mitsuhiro Goto、Kaori Tateishi、Kenki Ebine、Vadim A. Soloshonok、Christian Roussel、Osamu Kitagawa

  DOI：10.1016/j.tetasy.2016.03.004

  日期：2016.5