(+)-N-(benzoyl)-dehydroabietylamine | 35060-20-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (+)-N-(benzoyl)-dehydroabietylamine
• 英文别名: N-[[(1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methyl]benzamide
• CAS: 35060-20-9
• 化学式: C₂₇H₃₅NO
• 分子量: 389.581
• InChiKey: TUWHKPGGQKWBSS-DOEKTCAHSA-N

物化性质

• 沸点：
  547.3±19.0 °C(Predicted)
• 密度：
  1.032±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 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：

  (+)-N-(benzoyl)-dehydroabietylamine 在 chromium(VI) oxide 、 copper(II) nitrate trihydrate 作用下， 以 乙酸酐 、 溶剂黄146 为溶剂， 反应 66.0h， 生成 N-benzoyl-12-nitrodehydroabietylamine-7-one
  参考文献：
  名称：

  C7和C12官能化的脱氢松香胺衍生物的合成和抗衰老活性

  摘要：

  天然存在的或合成的Abietane型二萜类化合物已显示出广泛的药理作用，包括抗原生动物特性。在这项研究中，我们报告了一系列在C7和/或C12上官能化的（+）-脱氢松香胺衍生物的抗衰老性能评估。因此，该活性在体外针对婴儿利什曼原虫，杜氏利什曼原虫，利什曼原虫亚马孙和利什曼原虫guyanensis，进行了研究。大多数苯甲酰胺衍生物在低摩尔浓度下对利什曼原虫的前鞭毛体具有活性。（IC 50  = 2.2–46.8μM），对J774巨噬细胞无细胞毒性。化合物15，一种乙酰胺，尽管对J774细胞具有一定的细胞毒性，却被认为是最具活性的杀螨剂。在苯甲酰胺衍生物中，化合物8和10对婴儿乳杆菌细胞内的amastigotes也有活性，分别比参考化合物miltefosine的效力高18倍和23倍。对于这些脱氢松香胺衍生物中的抗菌活性，已经确定了一些构效关系。

  DOI：

  10.1016/j.ejmech.2016.06.004
• 作为产物：
  描述：

  氢化松香 、 苯甲酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以76%的产率得到(+)-N-(benzoyl)-dehydroabietylamine
  参考文献：
  名称：

  具有高强度和选择性活性的Abietane型二萜酰胺类化合物，可抵抗多形性利什曼原虫和克鲁氏锥虫

  摘要：

  以简单易行的方法，以脱氢松香胺（1）作为起始原料来合成一个小型的脱氢松香酰胺库，并测定了它们对两种引起疾病的锥虫（Leishmania donovani）和锥虫锥虫（Trypanosoma cruzi）的活性。已发现最有效的化合物10是脱氢松香胺和丙烯酸的酰胺，对这些寄生虫具有很高的效力，对杜氏诺森氏线虫无性变形虫的IC 50值为0.37μM，选择性指数为63。10个成分完全抑制多形利什曼原虫中胞内变形虫的生长IC 50值为0.06μM的人感染的巨噬细胞。该化合物还对L6细胞中存在的克鲁氏锥虫（T. cruzi amastigotes）高度有效，IC 50值为0.6μM ，高选择性指数为58，效力是参考化合物苯硝唑的3.5倍。该化合物的强效活性及其相对较低的细胞毒性使其对于进一步开发具有吸引力，以便为患有利什曼病和恰加斯病的患者寻求更好的药物。

  DOI：

  10.1021/acs.jnatprod.5b00990

文献信息

• Generation of Oxyphosphonium Ions by Photoredox/Cobaloxime Catalysis for Scalable Amide and Peptide Synthesis in Batch and Continuous‐Flow
  作者：Junqi Su、Jia‐Nan Mo、Xiangyang Chen、Alexander Umanzor、Zheng Zhang、Kendall N. Houk、Jiannan Zhao

  DOI：10.1002/anie.202112668

  日期：2022.1.26

  for the synthesis of amides and peptides is reported. Synergistic cooperation between a cobaloxime and a photoredox catalyst removes the elements of H2O through the use of PPh3 as a gentle organic reductant. The deoxygenative method is compatible with gram-scale peptide synthesis and applicable to peptide fragment condensation and SPPS, which may find applications in both organic synthesis and pharmaceutical

  报道了一种用于合成酰胺和肽的光催化方法。钴肟和光氧化还原催化剂之间的协同作用通过使用 PPh 3作为温和的有机还原剂去除了 H 2 O 元素。脱氧方法与克级肽合成兼容，适用于肽片段缩合和SPPS，可在有机合成和药物生产中找到应用。
• Compositions and methods relating to proliferative diseases
  申请人：The Penn State Research Foundation

  公开号：US09556101B2

  公开（公告）日：2017-01-31

  Anti-cancer compositions and methods are described herein. In particular, compositions including one or more of leelamine, a leelamine derivative, abietylamine, an abietylamine derivative, and an abietic acid derivative are described. Methods for treatment of pathological conditions particularly cancer, in a subject using one or more of leelamine, a leelamine derivative, abietylamine, an abietylamine derivative, and an abietic acid derivative are described herein.

  本文描述了抗癌组合物和方法。具体来说，描述了包含一种或多种利拉胺、利拉胺衍生物、阿比特胺、阿比特胺衍生物和松节酸衍生物的组合物。本文描述了利用一种或多种利拉胺、利拉胺衍生物、阿比特胺、阿比特胺衍生物和松节酸衍生物治疗病理条件，特别是癌症的方法。
• Phenacyl group containing amide derivative of dehydroabietylamine exhibiting enhanced cytotoxic activity against PLC and MCF7 cancer cell lines
  作者：Muhammad Ayaz Mustufa、Afshan Aslam、Cigdem Ozen、Imran Ali Hashmi、Naim ul Hasan Naqvi、Mehmet Ozturk、Firdous Imran Ali

  DOI：10.1007/s00044-017-1859-0

  日期：2017.7

  New amide derivatives of (+)-dehydroabietylamine, tricyclic abietane diterpene amine, were prepared using Zhongping's protocol. (+)-N-(2-phenyl-acetyl)-dehydroabietylamine derivative (11) demonstrated noticeable growth attenuation of hepatocellular carcinoma cell lines including PLC/PRF/5, SNU475, Hep3B-TR, and Huh7 with IC50 of 7.4 A mu M, 9.8 A mu M, 11.7 A mu M, and 11.8 A mu M, respectively. A breast cancer cell line MCF7 was the most sensitive against amide 11 with lowest IC50 value (4.8 A mu M). Low cell confluence and increase in G2/M phase was recorded after 48 and 72 h of treatment of amide 11 on PLC/PRF/5 cell line. Finally, amide 11 has comparatively sufficient therapeutic role due to addition of N-phenacyl group at C-18. Amide 11 demonstrated as potential candidate for future cancer interference and research.
• Syntheses of C-ring modified dehydroabietylamides and their cytotoxic activity
  作者：Jana Wiemann、Lucie Fischer、Matthias Rohmer、René Csuk

  DOI：10.1016/j.ejmech.2018.07.051

  日期：2018.8

  Due to their auspicious pharmacological efficacy as future drug candidates, natural products have been attracting scientific interest for centuries. An interesting field of research concerns the natural product class of terpenes. In this regard, a multitude of studies have already shown their promising biological potential. Therefore, a set of 27 derivatives of the diterpene dehydroabietylamine was synthesized, focusing on C-ring modifications and the derivatization of the amino moiety at C-18. Subsequent screening of the compounds in colorimetric sulforhodamine B-assays revealed an in vitro cytotoxicity especially towards malignant cell line MCF7. Particularly, 12-hydroxy-N-(isonicotinoyl)dehydroabietylamine and N-(4-methoxybenzoyl)dehydroabietylamine showed good cytotoxic activities (EC50 (MCF7) = 4.3 0.2 p,M and EC50 (MCF7) = 4.5 +/- 1.5 mu M, respectively) and significant selectivities (SI = 6.2 and SI = 8.8, respectively) towards malignant cell lines. (C) 2018 Elsevier Masson SAS. All rights reserved.
• Synthesis and antitumour activities of a novel class of dehydroabietylamine derivatives
  作者：Yong Chen、Zhong-Xiang Lin、Ai-Min Zhou

  DOI：10.1080/14786419.2011.648191

  日期：2012.12

  Structural modification is still a popular and important route in the forest chemical field for finding novel tricyclic diterpenes with more potential bioactivities and broad bioactive spectra. In this study, a series of dehydroabietylamine derivatives containing tricyclic diterpene structures were synthesised through oxidation in the 7th position of ring B and nitrification in the 12th position of ring C using dehydroabietylamine as the starting material. Structures of the synthesised compounds were confirmed by IR, H-1-NMR, C-13-NMR, MS and HRMS. The cytotoxicities of these compounds against PC-3 (human prostate carcinoma cell line) and Hey-1B (human ovarian carcinoma cell line) cells by the MTT assay were investigated. The results showed that the presence of a nitro group at 12th position and a carbonyl group at 7th position resulted in an increase of cytotoxic activity. Our findings present more evidence, showing the relationship between the chemical structure and biological function.