5893-29-8Relevant academic research and scientific papers
Design, Synthesis, and Insecticidal Activity of Novel Doramectin Derivatives Containing Acylurea and Acylthiourea Based on Hydrogen Bonding
Bai, Ping,Cheng, Yao,Lu, Xiaoxia,Yang, Jian,Zhang, Qi,Zheng, Cheng
, p. 5806 - 5815 (2020/06/19)
Our recent investigation on the insecticidal activities of several doramectin derivatives preliminarily revealed that the presence of hydrogen bonds at the C4″ position of the molecule with target protein γ-aminobutyric acid (GABA) receptor was crucial for retaining high insecticidal activity. As a continuation of our research work on the development of new insecticides, two series of novel acylurea and acylthiourea doramectin derivatives were designed and synthesized. The bioassay results indicated that the newly synthesized compounds (5o, 5t, and 6t) exhibited higher insecticidal activity against diamondback moth, oriental armyworm, and corn borer than the control compounds doramectin, commercial avermectins, chlorbenzuron, and lead compound 3g in our laboratory. Specifically, compound 5t was identified as the most promising insecticide against diamondback moth, with a final mortality rate of 80.00% at the low concentration of 12.50 mg/L, showing approximately 7.75-fold higher potency than the parent doramectin (LC50 value of 48.1547 mg/L), 6.52-fold higher potency than commercial avermectins (LC50 value of 40.5507 mg/L), and 3.98-fold higher potency than compound 3g (LC50 value of 24.7742 mg/L). Additionally, molecular docking simulations revealed that compound 5t (2.17, 2.20, 2.56, and 2.83 ?) displayed stronger hydrogen-bond action in binding with the GABA receptor, better than that of compound 5o (1.64 and 2.15 ?) and compound 6t (2.20 and 2.31 ?) at the C4″ position. This work demonstrated that these compounds containing hydrogen-bond groups might contribute to the improvement of insecticidal activity and supply certain hints toward structure optimization design for the development of new insecticides.
Convenient One-Pot Two-Step Synthesis of Symmetrical and Unsymmetrical Diacyl Ureas, Acyl Urea/Carbamate/Thiocarbamate Derivatives, and Related Compounds
Hernandez, Anolan Garcia,Grooms, Gregory M.,El-Alfy, Abir T.,Stec, Jozef
, p. 2163 - 2176 (2017/05/05)
A wide range of chemicals such as amides, hydrazides, amines, alcohols, carbazate, and sulfonate were reacted with acyl isocyanates generated by the reaction of primary amides with oxalyl chloride to give symmetrical and unsymmetrical diacyl urea derivatives, acyl ureas/carbamates/thiocarbamates, and related compounds. This method provides means for convenient one-pot, two-step synthesis of compounds bearing urea, carbamate, and other functional groups from cheap and commercially available starting reagents. It is expected that the results presented in this report will expand the medicinal chemist’s toolbox.
Design, synthesis and fungicidal activity of N-substituted benzoyl-1,2,3,4-tetrahydroquinolyl-1-carboxamide
Lei, Peng,Xu, Yan,Du, Juan,Yang, Xin-Ling,Yuan, Hui-Zhu,Xu, Gao-Fei,Ling, Yun
supporting information, p. 2544 - 2546 (2016/07/07)
To find a new lead compound with high biological activity, a series of N-substituted benzoyl-1,2,3,4-tetrahydroquinolyl-1-carboxamide were designed using linking active substructures method. The target compounds were synthesized from substituted benzoic acid by four steps and their structures were confirmed by 1H NMR, IR spectrum and elemental analysis. The in vitro bioassay results indicated that some target compounds exhibited excellent fungicidal activities, and the position of the substituents played an important role in fungicidal activities. Especially, compound 5n, exhibited better fungicidal activities than the commercial fungicide flutolanil against two tested fungi Valsa Mali and Sclerotinia sclerotiorum, with EC50 values of 3.44 and 2.63 mg/L, respectively. And it also displayed good in vivo fungicidal activity against S. sclerotiorum with the EC50 value of 29.52 mg/L.
Synthesis and antitumor activity of novel N-benzoyl-N'-substituted pyrimidinyl (thio)semicarbazide derivatives
Song, Gaopeng,Li, Jianzuo,Tian, Hao,Li, Yasheng,Hu, Dekun,Li, Ying,Cui, Zining
, p. 329 - 334 (2016/04/04)
A series of substituted pyrimidinyl (thio)semicarbazide derivatives were designed and synthesized. The antitumor results showed that the activity of thiosemicarbazide compounds (series II) was generally higher than that of the corresponding semicarbazide derivatives (series I). Among them, IIk displayed higher cytotoxicity against HL-60, BGC-823 and Bel-7402 than that of adriamycin and exhibited broad in vitro cytotoxicity against 13 human tumor cell lines. Meanwhile, the cytotoxic selectivity and anti-multidrug resistance were evaluated, and IIk exhibited selective cytotoxicity against cancer cells in comparison to human normal cells and had significant anti-multidrug resistance capability. The bioassay results showed that IIk showed great promise as a potent lead compound for further antitumor discovery.
Synthesis, structure and biological activity of some new aroylurea derivatives containing 1,3,4-thiadiazole
Song, Xin-Jian,Tan, Xiao-Hong
experimental part, p. 1755 - 1765 (2009/08/15)
In an extensive search for biologically active aroylurea compounds as plant growth regulators, a series of new N-aroyl-N′-[5-(E)-styryl-1,3,4- thiadiazol-2-yl]ureas have been designed and synthesized. Their structures were characterized by IR, 1H NMR, MS, elemental analysis, and single-crystal X-ray diffraction techniques. The preliminary bioassay showed that some of the title compounds exhibited good plant-growth regulating activity. Copyright Taylor & Francis Group, LLC.
CONDENSATION OF ACYL CHLORIDE ON SODIUM CYANATE : PREPARATION OF ACYL ISOCYANATES
Deng, M. Z.,Caubere, P.,Senet, J. P.,Lecolier, S.
, p. 6079 - 6086 (2007/10/02)
The catalytic effects of various metal halides and solvents on the reaction of benzoyl chloride with sodium cyanate were studied.It has been found that SnCl4, and ZnCl2 catalyze the reaction to give the corresponding acyl isocyanates in good yields.The scope of the reaction was studied and a number of aroyl isocyanates and their derivatives were prepared.A few non aromatic isocyanates and their derivatives were also prepared.
Reaction of Guanidinium Salts with Alkyl Bromides and Acid Chlorides
Kantlehner, Willi,Kapassakalidis, Johannis J.,Speh, Peter,Braeuner, Hans-Juergen
, p. 389 - 393 (2007/10/02)
The guanidinium salt 1a reacts with alkyl bromides 2a-g and acid chlorides 2h-k to give the nitriles 3a-g and the acyl cyanides 3h-k, respectively.Acyl isocyanates 4a,b have been obtained from the guanidinium cyanate 1d and the acid chlorides 2h,l.Reaction of the alkyl bromides 2b,c,m,n and acid chlorides 2h,l with the guanidinium thiocyanate 1e affords alkyl thiocyanates 5a-d and acyl isothiocyanates 6a,b, respectively.
