7-acetylharmol | 257938-78-6

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: 7-acetylharmol
• 英文别名: 7-acetyloxy-1-methyl-9H-pyrido[3,4-b]indole；1-methyl-9H-pyrido[3,4-b]indol-7-yl acetate；(1-methyl-9H-pyrido[3,4-b]indol-7-yl) acetate
• CAS: 257938-78-6
• 化学式: C₁₄H₁₂N₂O₂
• 分子量: 240.261
• InChiKey: SFZZHOSLBHIXJJ-UHFFFAOYSA-N

物化性质

• 沸点：
  455.4±40.0 °C(Predicted)
• 密度：
  1.312±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  55
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-acetylharmol 在 N-氯代丁二酰亚胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 3.0h， 生成 8-chloro-harmol
  参考文献：
  名称：

  溶液和固态中β-咔啉生物碱氯化制得的氯-β-咔啉的合成与分离

  摘要：

  在不同的实验条件下，β-咔啉（1-5）会被N-氯琥珀酰亚胺和N-氯苯并三唑进行亲电芳香取代。虽然6-氯和8-氯去甲harmane（1A和1B）和6-氯和8-氯harmane（图2a和2b中通过氯化与次氯酸钠去甲harmane获得）（1）和harmane （ 2）近期被分离出来并进行了全面表征，因此从未描述过正丁烷和异丁烷的其他氯代衍生物。二氯衍生物1c和1c的制备，后续分离，纯化和全面表征报告了2c（mp，R f，1 H nmr，13 C nmr和ms）以及从harmine （3a-3c），harmol （4a-4b ）获得的氯衍生物的制备，分离和表征）和7-乙酰基甘露醇（5a-5c）。作为溶液中的N-氯琥珀酰亚胺和N-氯苯并三唑以及β-咔啉-N-氯琥珀酰亚胺固体混合物作为氯化试剂，已经对其用途进行了比较。异丁烷的其他一氯衍生物的Gc（t R）和gc-ms（m / z）数据（1d）还包括痕

  DOI：

  10.1002/jhet.5570400304
• 作为产物：
  描述：

  肉叶云香碱 在 氢溴酸 、 三乙胺 作用下， 以 四氢呋喃 、 水 、 溶剂黄146 为溶剂， 反应 11.0h， 生成 7-acetylharmol
  参考文献：
  名称：

  Synthesis and Antiviral and Fungicidal Activity Evaluation of β-Carboline, Dihydro-β-carboline, Tetrahydro-β-carboline Alkaloids, and Their Derivatives

  摘要：

  Six known beta-carboline, dihydro-beta-carboline, and tetrahydro-beta-carboline alkaloids and a series of their derivatives were designed, synthesized, and evaluated for their anti-tobacco mosaic virus (TMV) and fungicidal activities for the first time. All of the alkaloids and some of their derivatives (compounds 3, 4, 14, and 19) exhibited higher anti-TMV activity than the commercial antiviral agent Ribavirin both in vitro and in vivo. Especially, the inactivation, curative, and protection activities of alkaloids Harmalan (62.3, 55.1, and 60.3% at 500 mu g/mL) and tetrahydroharmane (64.2, 57.2, and 59.5% at 500 mu g/mL) in vivo were much higher than those of Ribavirin (37.4, 36.2, and 38.5% at 500 mu g/mL). A new derivative, 14, with optimized physicochemical properties, obviously exhibited higher activities in vivo (50.4, 43.9, and 47.9% at 500 mu g/mL) than Ribavirin and other derivatives; therefore, 14 can be used as a new lead structure for the development of anti-TMV drugs. Moreover, most of these compounds exhibited good fungicidal activity against 14 kinds of fungi, especially compounds 4, 7, and 11.

  DOI：

  10.1021/jf404840x

文献信息

• Substituted beta-carbolines
  申请人：Aventis Pharma Deutschland GmbH

  公开号：EP1209158A1

  公开（公告）日：2002-05-29

  Compounds of the formula I are suitable for the production of pharmaceuticals for the prophylaxis and therapy of disorders in whose course an increased activity of IκB kinase is involved.

  式I的化合物适用于生产用于预防和治疗在其过程中涉及IκB激酶活性增加的疾病的药物。
• Synthesis and isolation of nitro-bT-carbolines obtained by nitration of commercial β-carboline alkaloids
  作者：María A. Ponce、Rosa Erra-Balsells

  DOI：10.1002/jhet.5570380510

  日期：2001.9

  Nitration of commercial full aromatic β-carboline alkaloids nor-harmane (1), harmane (2), harmine (3), harmol (4), and the 7-acetylated derivative of harmol (5) is described. Advantages and disadvantages of different nitration reagents which involve acidic conditions (HNO3/H+) and neutral conditions (Cu(NO3)2; ceric ammonium nitrate) are discussed. A complete 1H and 13C-nmr characterization including

  商用全芳香族β咔啉生物碱的硝化也不-harmane（1），harmane（2），去氢（3），harmol（4），和7-乙酰化衍生物harmol（的5）进行说明。讨论了涉及酸性条件（HNO 3 / H +）和中性条件（Cu（NO 3）2；硝酸硝酸铵）的不同硝化试剂的优缺点。完整的1 H和13给出了C-nmr表征，包括ms以及在中性和酸性介质中的uv吸收光谱。随函附上了详细的ei-ms和ld-tof-ms研究，因为硝基-β-咔啉构成了β-咔啉样生色团的新家族，并有可能在uv-maldi-tof-ms中用作基质。
• Synthesis and isolation of bromo-β-carbolines obtained by bromination of β-carboline alkaloids
  作者：María A. Ponce、Rosa Erra-Balsells

  DOI：10.1002/jhet.5570380512

  日期：2001.9

  2c, 2d, 2e are reported (mp, Rf, 1H-nmr, 13C-nmr and ms) together with the preparation, isolation and charaterization, for the first time, of the bromoderivatives obtained from harmine (3a-3e), harmol (4a, 4b) and 7-acetylharmol (5a-5c). As brominating reagent N-bromosuccinimide and N-bromosuccinimide-silica gel in dichloromethane and in chloroform as well as the β-carboline - N-bomosuccinimide solid

  在不同的实验条件下，β-咔啉（1-5）会被N-溴代琥珀酰亚胺进行亲电芳香取代。尽管前段时间通过溴化正六烷（1）溴化获得的6-溴-正六烷（1a）已被分离并完全表征，但正六烷（1b-1e）和harmane（2a-2e）的其他溴代衍生物部分被描述为反应混合物的一部分。报告了1b，1c，1d，1e，2a，2b，2c，2d，2e的制备以及随后的分离，纯化和完整表征（mp，R f，1 H-nmr，13C-nmr和ms）以及从harmine（3a-3e），harmol（4a，4b）和7-乙酰基harmol （5a-5c）获得的溴代衍生物的首次制备，分离和表征。作为溴化剂Ñ溴代琥珀酰亚胺和Ñ溴代琥珀酰亚胺硅胶在二氯甲烷和氯仿中，以及在β咔啉- ñ -bomosuccinimide固体混合物已被用于和其用途进行了比较。进行了半经验的AMI和PM3计算，以便根据HOMO的能量，HOMO-LUMO的差异以及β-
• Antitumor agents 201.1 Cytotoxicity of harmine and β-carboline analogs
  作者：Junko Ishida、Hui-Kang Wang、Kenneth F. Bastow、Chang-Qi Hu、Kuo-Hsiung Lee

  DOI：10.1016/s0960-894x(99)00598-3

  日期：1999.12

  Twenty-six beta-carbolines were evaluated for in vitro cytotoxicity in a human tumor cell line panel. Harmine (3) showed significant activity against several cell lines including three drug-resistant KB sublines with various resistance mechanisms. alpha-(4-Nitrobenzylidine) harmine (16) had a broad cytotoxicity spectrum (ED50 values from 0.3-1.2 mu g/mL against 1A9, KB, SaOS-2, A549, SK-MEL-2, U-87-MG, and MCF-7 cells). (C) 1999 Published by Elsevier Science Ltd. All rights reserved.
• Extracts of Cranberry and Methods of Using Thereof
  申请人：Alberte Randall S.

  公开号：US20100028469A1

  公开（公告）日：2010-02-04

  The present disclosure relates in part to extracts of cranberry ( Vaccinium macrocarpon ) comprising an enriched amount of certain compounds having anti-infective activity, e.g. antibacterial and/or antifungal activity, e.g. activity against C. albicans . Another aspect of the disclosure relates to combined cranberry and cinnamon extracts. In certain embodiments, these combined extracts have been optimized to control urinary tract infections caused by E. coli, S. aureus and C. albicans . Certain embodiments of the extract are enriched in bioactive compounds that have been shown to inhibit C. albicans adhesion and/or biofilm formation and its growth in vitro. In another aspect of the disclosure, the extracts are enriched in bioactives derived from cranberry and cinnamon that have been shown to inhibit the attachment and the growth of common urinary tract pathogens like E. coli, S. aureus and C. albicans.

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