40624-43-9Relevant articles and documents
Iodine-Mediated Domino Cyclization for One-Pot Synthesis of Indolizine-Fused Chromones via Metal-Free sp3C-H Functionalization
Zhang, Xiang-Jin,Wang, Zhuo,Zhang, Han,Gao, Jing-Jing,Yang, Kai-Rui,Fan, Wei-Yu,Wu, Rui-Xue,Feng, Meng-Lin,Zhu, Wei,Zhu, Yan-Ping
, p. 835 - 845 (2022/01/12)
An efficient method for the synthesis of new indolizine-fused chromones has been accomplished from ethyl (E)-3-(2-acetylphenoxy)acrylates and pyridines in a "one-pot"manner. Facile operation in open-air, metal-free, and mild conditions renders this protocol particularly practical and attractive. Moreover, this method can simultaneously construct two molecular fragments of chromone and indolizine. Scale-up experiment and the construction of natural products further prove the practicability of this strategy.
Full Color Tunable Aggregation-Induced Emission Luminogen for Bioimaging Based on an Indolizine Molecular Framework
Choi, Sang-Kee,Rho, Jungi,Yoon, Sang Eun,Seok, Jin-Hong,Kim, Hyungi,Min, Junsik,Yoon, Woojin,Lee, Sanghee,Yun, Hoseop,Kwon, O-Pil,Kim, Jong H.,Kim, Wook,Kim, Eunha
, p. 2522 - 2532 (2020/12/18)
By taking advantage of a unique mechanism of aggregation-induced emission (AIE) phenomena, AIE luminogens (AIEgens) have been provided as a solution to overcome the limitations of conventional fluorophores bearing the feature of aggregation-caused quenching (ACQ) phenomena. Especially, AIEgens paved the way to develop fluorogenic probes ideal for fluorescent imaging in live cell conditions. Despite the high demand for discovery of new AIEgens, it is still challenging to find a versatile molecular platform to generate diverse AIEgens. Herein, we report a new colorful molecular framework, Kaleidolizine (KIz), as a molecular platform for AIEgen generation. The KIz system allows systematic tuning of the emission wavelength from 455 to 564 nm via perturbation of the electron density of substituents on the indolizine core. Increasing the water fraction of the KIz solution in the THF/water mixture induces the fluorescence intensity increase up to 120-fold. Crystal structure analysis, computational calculations, and solvatochromism studies suggest that a synergistic effect between the intramolecular charge transfer and restriction of intramolecular rotation acts as the AIE mechanism in the KIz system. Conjugation of the triphenylphosphonium moiety to KIz allows successful development of triphenylphosphonium (TPP)-KIz for real-time bioimaging of innate mitochondria in live cells, thereby revealing the potential of KIz as a versatile molecular platform to generate fluorogenic probes based on AIE phenomena. We do believe the KIz system could serve as a new, reliable, and generally applicable molecular platform to develop various AIEgens having desired photophysical properties along with an excellent signal-to-noise ratio and with experimental convenience especially for fluorogenic live cell imaging.
Iodine-Mediated Oxidative Cyclization of 2-(Pyridin-2-yl)acetate Derivatives with Alkynes: Condition-Controlled Selective Synthesis of Multisubstituted Indolizines
He, Lisheng,Li, Chunyan,Liang, Guangyan,Liu, Xiaolan,Pan, Weidong,Wang, Daoping,Yang, Yuzhu
supporting information, p. 459 - 470 (2020/01/23)
An iodine-mediated oxidative cyclization reaction between 2-(pyridin-2-yl)acetate derivatives and different alkynes has been developed, which provides regioselective and chemoselective syntheses of multiply substituted indolizines under modified reaction
Pyrrolo-nitrogen bridge aromatic compound and preparation method thereof
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Paragraph 0038-0040, (2020/01/08)
The invention discloses a pyrrolo-nitrogen bridge aromatic compound and a preparation method thereof. The compound is obtained by adding a pyridine compound II and ethyl acrylate or methyl acrylate into a solvent, then adding a catalyst and alkali, and pe
Iodine-mediated one-pot synthesis of C-3 acylated indolizines from pyridines, aryl methyl ketones and acrylate derivatives
Fang, Youlai,He, Lisheng,Pan, Weidong,Yang, Yuzhu
supporting information, p. 3767 - 3771 (2019/06/08)
An I2/CuI-promoted multi-component reaction from pyridines, aryl methyl ketones and electron deficient acrylates has been accomplished in a “one-pot” manner, which provides a straightforward and efficient access to C-3 acylated indolizines. The
Catalyst-Free Annulation of 2-Pyridylacetates and Ynals with Molecular Oxygen: An Access to 3-Acylated Indolizines
Chen, Zhengwang,Liang, Pei,Ma, Xiaoyue,Luo, Haiqing,Xu, Guohai,Liu, Tanggao,Wen, Xiaowei,Zheng, Jing,Ye, Hui
, p. 1630 - 1639 (2019/01/26)
A catalyst and additive-free annulation of 2-pyridylacetates and ynals under molecular oxygen was the first developed, affording 3-acylated indolizines in good to excellent yields. Molecular oxygen was used as the source of the carbonyl oxygen atom in indolizines. This approach was compatible with a wide range of functional groups, and especially it has been successfully extended to unsaturated double bonds and triple bonds, which were difficult to prepare by previous methods in a single step.
Preparation method of C-3 arylformylindolizine compounds
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Paragraph 0030-0033; 0036; 0039; 0041-0050, (2019/09/16)
The invention discloses a preparation method of C-3 arylformylindolizine compounds. The method comprises the following steps: adding a metal additive, elemental iodine, a pyridine derivative, aromaticethanone, an electron deficient olefin and a base into
Transition-Metal-Free Synthesis of Indolizines from Electron-Deficient Alkenes via One-Pot Reaction Using TEMPO as an Oxidant
Shi, Fei,Zhang, Yu,Lu, Zhaole,Zhu, Xiaolei,Kan, Weiqiu,Wang, Xiang,Hu, Huayou
, p. 413 - 420 (2016/01/28)
A one-pot method for the synthesis of multisubstituted indolizines from α-halo carbonyl compounds, pyridines, and electron-deficient alkenes is reported. The oxidative dehydrogenation reaction takes place under transition-metal-free conditions using TEMPO as an oxidant. This protocol uses ready available starting materials in a convenient procedure under mild reaction conditions.
Synthesis and biological activities of indolizine derivatives as alpha-7 nAChR agonists
Xue, Yu,Tang, Jingshu,Ma, Xiaozhuo,Li, Qing,Xie, Bingxue,Hao, Yuchen,Jin, Hongwei,Wang, Kewei,Zhang, Guisen,Zhang, Liangren,Zhang, Lihe
, p. 94 - 108 (2016/04/05)
Human α7 nicotinic acetylcholine receptor (nAChR) is a promising therapeutic target for the treatment of schizophrenia accompanied with cognitive impairment. Herein, we report the synthesis and agonistic activities of a series of indolizine derivatives targeting to α7 nAChR. The results show that all synthesized compounds have affinity to α7 nAChR and some give strong agonistic activity, particularly most active agonists show higher potency than control EVP-6124. The docking and structure-activity relationship studies provide insights to develop more potent novel α7 nAChR agonists.
Novel indolizine derivatives with unprecedented inhibitory activity on human farnesyltransferase
Dumea, Carmen,Belei, Dalila,Ghinet, Alina,Dubois, Jolle,Farce, Amaury,Bcu, Elena
, p. 5777 - 5781 (2015/01/08)
The rational structural modification of new substituted indolizin-3-yl(phenyl)methanones 1a-i, 2a-i and 3a-i has greatly improved human farnesyltransferase inhibition. The para-bromophenyl analog 2f bearing an ester unit on the indolizine ring demonstrates the highest inhibition potential, with IC50 value of 1.3 ± 0.2 μM. The amidic series 1a-i proves to be the most promising for future modulations, particularly at the triple bond level.
