- Synthesis, molecular modeling, selective aldose reductase inhibition and hypoglycemic activity of novel meglitinides
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In the present study, a novel generation of selective aldose reductase ALR2 inhibitors with significant hypoglycemic activities was designed and modulated based on rhodanine scaffold joined to an acetamide linker in between two lipophilic moieties. The synthesis of the novel compounds was accomplished throughout simple chemical pathways. Molecular docking was performed on B-cell membrane protein SUR1, aldehyde reductase ALR1 and aldose reductase ALR2 active sites. Compounds 10B, 11B, 12B, 15C, 16C, 26F and 27F displayed the highest hypoglycemic activities with 80.7, 85.2, 87, 82.3, 83.5, 81.4 and 85.3% reduction in blood glucose levels, respectively. They were more potent than the standard hypoglycemic agent repaglinide with 65.4% reduction in blood glucose level. Compounds 12B and 15C with IC50 0.29 and 0.35 μM were more potent than the standard ALR2 inhibitor epalrestat with IC50 0.40 μM. They were selective towards ALR2 over ALR1 134 and 116 folds, respectively. Molecular docking studies matched with the in-vitro and in-vivo results to elucidate the dual activities of both compounds 12B and 15C as potent antagonists for ALR2 over ALR1 and good agonists for the SUR1 protein.
- Salem, Manar G.,Abdel Aziz, Yasmine M.,Elewa, Marwa,Nafie, Mohamed S.,Elshihawy, Hosam A.,Said, Mohamed M.
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- Introducing broadened antibacterial activity to rhodanine derivatives targeting enoyl-acyl carrier protein reductase
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Broadened antibacterial activity was introduced to rhodanine derivatives targeting Mycobacterial tuberculosis enoyl-acyl carrier protein reductase (Mtb InhA) by recruiting feature of xacins to bring DNA Gyrase B inhibitory capability. This is significant for preventing further bacterial injections in the tuberculosis treatment. The most potent compound Cy14 suggested comparable bioactivity (IC50=3.18μM for Mtb InhA; IC50=10nM for DNA Gyrase B) with positive controls. Structure–activity relationship discussion and molecular docking model revealed the significance of rhodanine moiety and derived methoxyl on meta-position, pointing out orientations for future modification.
- Sun, Zhi-Gang,Xu, Yun-Jie,Xu, Jian-Fei,Liu, Qi-Xing,Yang, Yu-Shun,Zhu, Hai-Liang
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p. 125 - 129
(2019/03/28)
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- Green synthesis of 5 arylidene-2,4-thiazolidinedione, 5-benzylidene rhodanine and dihydrothiophene derivatives catalyzed by hydrated ionic liquid tetrabutylammonium hydroxide in aqueous medium
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An efficient synthesis of 5 arylidene-2,4-thiazolidinediones and 5-benzylidene rhodanines by the Knoevenagel condensation of 2,4- thiazolidinedione or rhodanine with aromatic aldehydes was studied. It proceeded smoothly in the presence of tetrabutylammonium hydroxide/H2O-EtOH to afford the corresponding products in high yields at 50C. Also, a series of dihydrothiophene derivatives were synthesized via the four-component reaction of aldehyde, malonitrile, 2,4-thiazolidinedione, and piperidine in the presence of Bu4NOH as a basic ionic liquid in aqueous medium. This new method offers several advantages, such as excellent yields, short reaction times, and simple procedure(Equation presented). 2013
- Khazaei, Ardeshir,Veisi, Hojat,Safaei, Maryam,Ahmadian, Hossein
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p. 270 - 278
(2014/04/03)
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- Urea/thiourea catalyzed, solvent-free synthesis of 5-arylidenethiazolidine- 2,4-diones and 5-arylidene-2-thioxothiazolidin-4-ones
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An efficient and organo-catalyzed method has been developed for the synthesis of 5-arylidenethiazolidine-2,4-diones and 5-arylidene-2- thioxothiazolidin-4-ones via Knoevenagel condensation of arylaldehydes 1 and 2,4-thiazolidinedione 2a/2-thioxothiazolidin-4-one 2b under mild conditions. Urea-adduct 4 and azomethine 5 also afford arylidene-products 3 by reacting with 2a-b via addition-elimination reaction. This protocol has the features of use of inexpensive, ecofriendly readily available, effective catalyst system viz. urea/thiourea, avoidance of volatile solvents, excellent yield and simple work-up procedure.
- Shah, Sakshi,Singh, Baldev
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experimental part
p. 5388 - 5391
(2012/09/22)
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- A solvent-free protocol for the green synthesis of arylalkylidene rhodanines in a task-specific ionic liquid
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2-Hydroxyethylammonium formate acts as a task-specific ionic liquid (TSIL) for the Knoevenagel condensation of carbonyl compounds with rhodanine to afford arylalkylidene rhodanines under solvent-free conditions and in good-to-excellent yields. Additionally, compared with those in organic solvents, the yields obtained in the presence of our ionic liquid (IL) were significantly increased. The detailed mechanism of the catalytic effect of TSIL is also reported for the first time.
- Alizadeh, Abdolhamid,Khodaei, Mohammad M.,Eshghi, Ali
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experimental part
p. 514 - 518
(2010/08/04)
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- Iodine catalysed synthesis of 5-(arylmethylidene)rhodanines by grinding under solvent-free conditions
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5-(Arylmethylidene)rhodanines have been synthesised in 88-95% yields by Knoevenagel condensation of various aromatic aldehydes with rhodanine in the presence of a catalytic amount of iodine at room temperature by grinding under solvent-free conditions.
- Wang, Hongshe,Zeng, June
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experimental part
p. 374 - 376
(2009/12/31)
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- Green synthesis of 5-benzylidene rhodanine derivatives catalyzed by 1-butyl-3-methyl imidazolium hydroxide in water
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A basic functionalized ionic liquid, 1-butyl-3-methyl imidazolium hydroxide ([bmim][OH]), catalyzed the Knoevenagel condensation of rhodanine with aromatic aldehydes. It proceeded smoothly in water to afford the 5-benzylidene rhodamine derivatives in high yields at room temperature. This new method offers several advantages, such as excellent yields, short reaction times, and simple procedure. The catalyst can be reused at least 5 times without significant loss of activity.
- Gong, Kai,He, Zhi-Wei,Xu, Ying,Fang, Dong,Liu, Zu-Liang
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experimental part
p. 913 - 915
(2009/09/06)
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- Facile synthesis of 5-benzylidene rhodamine derivatives under microwave irradiation
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A series of 5-benzylidenerhodamine derivatives were synthesized by the cross-aldol condensation of an aromatic aldehyde with rhodamine or rhodamine acetic acid in sodium acetate/acetic acid under microwave irradiation. The reaction was completed in 8-20 min with 63-94% yields and was environmentally benign with easy workup. Copyright Taylor & Francis Group, LLC.
- Zhou, Jian-Feng,Song, Yuan-Zhi,Zhu, Feng-Xia,Zhu, Yu-Lan
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p. 3297 - 3303
(2007/10/03)
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- Efficient synthesis of 3-acyl-5-arylmethylene-4-oxothiazolidine-2-thiones
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An efficient procedure was suggested for preparing 3-acyl-5-arylmethylene- 4-oxothiazolidine-2-thiones.
- Aronova,Ginak
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p. 164 - 165
(2007/10/03)
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- Synthesis and nonlinear optical properties of p-(dimethylamino)benzylidene dyes containing different acceptors
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Several p-(dimethylamino)benzylidene dyes were synthesized and their evaluation of β using Hyper-Rayleigh Scattering (HRS) technique was reported. The results show that these dyes have enhanced second-order hyperpolarizabilities.
- Zheng, Qingdong,Yao, Zuguang,Cheng, Jiqi,Shen, Yaochun,Lu, Zuhong
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p. 1426 - 1427
(2007/10/03)
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