3-Nitrocytisine | 267401-42-3

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 羽扇豆生物碱
• 英文名称: 3-Nitrocytisine
• 英文别名: 9-nitrocytisine；(1R,5S)-9-Nitro-3,4,5,6-tetrahydro-1H-1,5-methanopyrido[1,2-a][1,5]diazocin-8(2H)-one；(1R,9S)-5-nitro-7,11-diazatricyclo[7.3.1.02,7]trideca-2,4-dien-6-one
• CAS: 267401-42-3
• 化学式: C₁₁H₁₃N₃O₃
• 分子量: 235.243
• InChiKey: TYIJTKJEBUZNGQ-JGVFFNPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  78.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-Nitrocytisine 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以100%的产率得到(-)-(1R,5S)-9-amino-1,2,3,4,5,6-hexahydro-1,5-methano-pyrido[1,2-a][1,5]diazocin-8-one
  参考文献：
  名称：

  Synthesis of Analogues of (−)-Cytisine for in Vivo Studies of Nicotinic Receptors Using Positron Emission Tomography

  摘要：

  9-Substituted analogues of (-)-cytisine were synthesized in high yields via palladium-mediated couplings of either 9- (-)-bromocytisine and organostannanes or 9-(-) trimethylstannylcytisine and fluorobromobenzene. The protection of the amine with a nitroso group and the use of PdCl2(PPh3)(2) to carry out the Stille reaction allowed the rapid synthesis of 9-(4'-[F-18]fluorophenyl)cytisine (F-18: t(1/2) = 109.7 min), a new promising radioligand (radiochemical yield: 10% from [F-18]KF, 150 min, four steps) for positron emission tomography studies of alpha(4)beta(2) nicotinic receptors.

  DOI：

  10.1021/ol005685m
• 作为产物：
  描述：

  cytisine 在 硫酸 、 硝酸 作用下， 反应 2.0h， 以55%的产率得到3-Nitrocytisine
  参考文献：
  名称：

  改性香豆素。40. 9-Nitrocytisine 的苯并吡喃-2-一羰基衍生物的合成

  摘要：

  合成了含有 9-硝基胞嘧啶部分的香豆素、呋喃香豆素和二氢吡喃香豆素的衍生物。

  DOI：

  10.1007/s10600-017-2020-5

文献信息

• Cytisine-flavonoid conjugates: Synthesis and antitumor structure-activity relationship research
  作者：Renhao Liu、Xiaoze Bao、Xuanrong Sun、Yue Cai、Tianwei Zhang、Xinyi Ye、Xing-Nuo Li

  DOI：10.1016/j.tetlet.2020.151803

  日期：2020.4

  In research of anti-triple negative breast cancer (TNBC) agents, a series of cytisine-flavonoid conjugates (A-1∼G-1) were designed and synthesized in high yields with (-)-cytisine and flavonoids via N,N-4-dimethyl-4-aminopyridine (DMAP)-catalyzed synthetic strategy. In addition, the in vitro cytotoxicity of the conjugates was tested, and the results showed that some compounds had better cytotoxicity

  在抗三阴性乳腺癌（TNBC）剂的研究，一系列金雀花碱的类黄酮共轭物（的A-1~G-1 ）设计并以高产率合成了（ - ） -金雀花碱和黄酮类化合物经由N，N- - 4-二甲基-4-氨基吡啶（DMAP）催化的合成策略。另外，测试了缀合物的体外细胞毒性，结果表明某些化合物对人乳腺癌细胞（MDA-MB-231）的毒性比阳性对照药物紫杉醇更好。结构-活性关系的研究表明，以5-氯和黄酮类为特征的半胱氨酸形成的结合物对MDA-MB-231细胞具有更好的抗增殖作用。
• Exploring bulky natural and natural-like periphery in the design of p-(benzyloxy)phenylpropionic acid agonists of free fatty acid receptor 1 (GPR40)
  作者：Sergey O. Kuranov、Olga A. Luzina、Oleksandra Onopchenko、Iryna Pishel、Sergey Zozulya、Maxim Gureev、Nariman F. Salakhutdinov、Mikhail Krasavin

  DOI：10.1016/j.bioorg.2020.103830

  日期：2020.6

  acid receptor 1 (FFA1) activation. Two frontrunner compounds (bearing a bornyl and cytosine groups) were evaluated in an oral glucose tolerance test in mice where both demonstrated the ability to sustain blood glucose levels following a glucose challenge. The bornyl compound displayed a somewhat superior, dose-dependent efficacy and, therefore, can be regarded as a lead compounds for further development

  合成了具有各种天然和类似天然的，在空间上定义的外围基序的3-苯基丙酸的六种衍生物，并在体外评估了游离脂肪酸受体1（FFA1）的活化。在小鼠的口服葡萄糖耐量试验中评估了两种领先的化合物（带有冰片基和胞嘧啶基团），其中两种化合物均显示出在葡萄糖激发后能够维持血糖水平的能力。冰片基化合物显示出更好的剂量依赖性功效，因此，可以被认为是进一步开发的先导化合物，作为2型糖尿病的治疗剂。通过对接实验使它对FFA1的高亲和力合理化。
• Antiviral activity of amides and carboxamides of quinolizidine alkaloid (−)-cytisine against human influenza virus A (H1N1) and parainfluenza virus type 3
  作者：Victoria A. Fedorova、Renata A. Kadyrova、Alexander V. Slita、Anna A. Muryleva、Polina R. Petrova、Alena V. Kovalskaya、Alexander N. Lobov、Zulfiya R. Zileeva、Dmiry O. Tsypyshev、Sophia S. Borisevich、Inna P. Tsypysheva、Julia V. Vakhitova、Vladimir V. Zarubaev

  DOI：10.1080/14786419.2019.1696791

  日期：2021.11.17

  derivatives obtained from allyl isocyanate and (−)-cytisine or 9,11-dibromocytisine are able to inhibit a reproduction of HPIV3 with SI = 58 and 95. Moreover, last compound - (1 R,5R)-N-allyl-9,11-dibromo-8-oxo-1,5,6,8-tetrahydro-2H-1,5-methanopyrido[1,2-a][1,5]diazocine-3(4H)-carboxamide with two bromine atom in 2-pyridone core of starting (−)-cytisine molecule, demonstrated high activity against HPIV3

  摘要 合成了喹唑啉生物碱 ( - )-胞嘧啶的新型衍生物。评估了 ADME 特性、对 HEK293 细胞的细胞毒性和对 A/California/07/09(H1N1)pDM09 病毒 (IAV) 和人类副流感病毒 3 (HPIV3) 病毒的活性。结果表明，甲基胞嘧啶的 9-甲酰胺（带有苯基和烯丙基脲的片段）是对 IAV 最具活性的化合物，这可能是由于计算机预测的它们与 IAV 神经氨酸酶的 4R7B 活性位点相互作用的特殊性。以这些尿素的CC 50 /IC 50之比计算的选择性指数(SI)相应地为47和59。还发现，从异氰酸烯丙酯和 ( -)-cytisine 或 9,11-dibromocytisine 能够抑制 HPIV3 的繁殖，SI = 58 和 95。此外，最后一种化合物 - (1  R ,5 R )- N -allyl-9,11-dibromo-8-oxo -1,5,6,8-tetrahydro-2
• New 12-N-β-Hydroxyethylcytisine Derivatives with Potential Antiarrhythmic Activity
  作者：I. P. Tsypysheva、A. V. Koval’skaya、I. U. Khalilova、Yu. Yu. Bakhtina、R. Yu. Khisamutdinova、S. F. Gabdrakhmanova、A. N. Lobov、F. S. Zarudii、M. S. Yunusov

  DOI：10.1007/s10600-014-0945-5

  日期：2014.5

  12-N-β-Hydroxyethylcytisine derivatives containing Cl, Br, and nitro groups on the 2-pyridone core were synthesized. Their antiarrhythmic activity was studied in vivo.

  研究人员合成了在 2-吡啶酮核心上含有 Cl、Br 和硝基的 12-N-β-羟乙基胞嘧啶衍生物。在体内研究了它们的抗心律失常活性。
• Synthesis and Cytotoxic Activity of Conjugates of (–)-Cytisine and Thermopsin Amine Derivatives with 1,3-Dimethyl-5-Formyluracil
  作者：I. P. Tsypysheva、P. R. Petrova、A. V. Koval’skaya、A. N. Lobov、M. A. Maksimova、L. F. Zainullina、V. I. Vinogradova、V. A. Vakhitov、Yu. V. Vakhitova、F. Z. Galin

  DOI：10.1007/s10600-018-2517-6

  日期：2018.9

  New conjugates of the quinolizidine alkaloids (–)-cytisine and thermopsin were synthesized by alkylating their 9-amino derivatives with 1,3-dimethyl-5-formyluracil. The cytotoxic properties of the synthesized conjugates against cell lines HEK293, HepG2, and Jurkat were studied. Screening identified the lead compound 5-[(3-benzyl-8-oxo-1,3,4,5,6,8-hexahydro-2H-1,5-methanopyrido[1,2-a][1,5]diazocin

  通过用 1,3-二甲基-5-甲酰尿嘧啶对它们的 9-氨基衍生物进行烷基化，合成了喹尼西啶生物碱 (-)-胞嘧啶和嗜热蛋白酶的新结合物。研究了合成的缀合物针对细胞系 HEK293、HepG2 和 Jurkat 的细胞毒性特性。筛选确定了先导化合物 5-[(3-benzyl-8-oxo-1,3,4,5,6,8-hexahydro-2H-1,5-methanopyrido[1,2-a][1,5 ]diazocin-9-yl)amino]methyl}-1,3-dimethylpyrimidine-2,4-(1H,3H)-dione，抑制淋巴细胞白血病细胞的代谢活性，抑制浓度 (IC50) 20.6 ± 2.1 μM (IC50参考化合物 5-氟尿嘧啶的浓度为 18.5 ± 3.3 μM)。