80360-20-9Relevant academic research and scientific papers
First discovery of pimprinine derivatives and analogs as novel potential herbicidal, insecticidal and nematicidal agents
Zhang, Ming-Zhi,Mulholland, Nick,Seville, Anne,Hough, Gemma,Smith, Nicholas,Dong, Hong-Qiang,Zhang, Wei-Hua,Gu, Yu-Cheng
, (2020/12/21)
Pimprinine and streptochlorin are indole natural products produced by many species of organisms, and they are reported to possess a wide range of biological activities, such as anticancer, antiviral, antifungal activity and so on. In this study, three series of pimprinine derivatives or analogs were efficiently synthesized under the optimized methods. Biological assays conducted at Syngenta firstly indicated the pimprinine derivatives or analogs possessed potential herbicidal and insecticidal activity, and this is highlighted by compounds 21g, 21h, 21i, 21j, 21l, 22h, 22i and 23h, they possessed significant biological activity as well as broad spectrum. Meanwhile, compounds with benzothiophene-oxazole core (21h, 22h and 23h), showed effective nematicidal activity in primary screening. Compounds 21g and 21i were identified as the most promising lead structures for further study.
Design, synthesis, stereochemical determination, molecular docking study, in silico pre-ADMET prediction and anti-proliferative activities of indole-pyrimidine derivatives as Mcl-1 inhibitors
Lamie, Phoebe F.,Philoppes, John N.
, (2021/09/14)
In this study, fourteen novel indole-pyrimidine hybrids were designed and synthesized. Their chemical structures were confirmed using different spectroscopic techniques (1H NMR, 13C NMR, IR and mass). Their (E) stereochemical configuration was determined theoretically (MM2 property) and experimentally using 2D NMR technique (NOESY experiment). The prepared compounds were subjected to preliminary biological studies as Mcl-1 inhibitors. Most of the compounds exhibited good abilities for targeting Mcl-1 protein, especially, 7d, 7e, 7i and 7k (Ki = 11.19–15.21 nM). These derivatives were further evaluated against Bcl-XL and Bcl-2 proteins. Some compounds were found to have dual Mcl-1/Bcl-XL such as 7i, or Bcl-XL/Bcl-2 inhibitory activity as 7d. The most potent derivatives as Mcl-1 inhibitors were chosen as representative examples for determination of in-vitro anti-proliferative activity against PC-3, K-562 and MDA-MB-231 cell lines. They possessed excellent to good anti-proliferative activities. All of the synthesized compounds were docked into Mcl-1 active site. Drug-likeness properties and in silico pre-ADMET characters were also predicted.
Synthesis, antimycobacterial and anticancer activity of novel indole-based thiosemicarbazones
Mashayekhi, Vida,Haj Mohammad Ebrahim Tehrani, Kamaleddin,Azerang, Parisa,Sardari, Soroush,Kobarfard, Farzad
, (2021/09/08)
Based on the structural elements of bioactive indole-based compounds, a series of novel 1-substituted indole-3-carboxaldehyde thiosemicarbazones were synthesized as potential antimycobacterial and anticancer agents. The derivatives were prepared via a two
Preparation method and application of natural product Streptochlorin and derivatives thereof
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, (2020/07/12)
The invention discloses a preparation method of a derivative of a natural product Streptochlorin. The invention also discloses an application of the natural product Streptochlorin and the derivative thereof in killing pathogenic bacteria of crops. The natural product Streptochlorin and the derivative thereof have the advantages that the bactericidal activity is good, can be applied to crop diseases caused by fungi, bacteria and viruses, and show efficient and/or broad-spectrum bactericidal activity.
Synthesis and Antiproliferative Activity of New N-Acylhydrazone Derivatives Containing Benzothiazole and Indole Based Moiety
Ding, Yangyang,Kang, Congmin,Liu, Kai
, p. 345 - 352 (2020/07/30)
Through a structure-based molecular hybridization strategy, a series of new N-acylhydrazone derivatives containing the benzothiazole and indole based moiety were designed, synthesized and screened for in vitro antiproliferative activity against Hep G2 cancer cell line. One compound (7a) exhibited excellent antiproliferative activity with IC50 values of 0.78 μM against Hep G2. In addition, C-5 substitutions of the indole ring of target compounds might be crucial for their cytotoxic activities. Additionally, the relative configuration of target compounds was confirmed as the E isomer. Further chemical manipulation of derivative 7a can make it possible to obtain new potential antitumor agents.
Synthesis, antimicrobial and cytotoxic activities, and molecular docking studies of N-arylsulfonylindoles containing an aminoguanidine, a semicarbazide, and a thiosemicarbazide moiety
Song, Mingxia,Wang, Shiben,Wang, Zengtao,Fu, Zhiyang,Zhou, Shengchao,Cheng, Huabin,Liang, Zhuo,Deng, Xianqing
, p. 108 - 118 (2019/01/28)
Thirty-six N-arylsulfonyl-3-substituted indoles were designed and synthesized by combining the N-arylsulfonylindoles with aminoguanidine, semicarbazide, and thiosemicarbazide, respectively. Their antibacterial activities were screened, and cytotoxic activities were evaluated. The results showed that aminoguanidines (6) exhibited much better antibacterial activity than semicarbazides (7) and thiosemicarbazides (8). Most compounds in series 6 showed potent inhibitory activity against the tested bacterial strains, including multidrug-resistant strains, with MIC values in the range of 1.08–23.46 μM. The cytotoxic activity of the compounds 6c, 6d, 6h, 6j, 6k and 6l was assessed in two human cancer cell lines A590 and SGC7901, and one human normal cell line HEK 293T. The results indicated that compounds selected exhibited excellent activity against the tested cancer cells with IC50 values in the range of 1.51–15.12 μM suggesting the potential of them as new antibacterial and anticancer agents. What's more, the results of resistance study revealed that resistance of the tested bacteria toward 6d is not easily developed. Molecular docking studies revealed that the aminoguanidine and arylsulfonylindole moieties played a significant role in binding the target site of E. coli FabH-CoA receptor.
Synthesis of an azide-tethered 4H-furo[3,4-b]indole
Keavy, Daniel J.,Liu, Yanbing,Gribble, Gordon W.
, p. 368 - 375 (2020/02/13)
We describe the synthesis of a novel azide-tethered 4H-furo[3,4-b]indole as a putative intermediate for a projected route to the 2-acylindole class of indole alkaloids. O N3 Me N N N H N H H O
2-(indol-3-yl)-pyridinoimidazole and application thereof
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Paragraph 0023-0028, (2019/06/07)
The invention relates to a 2-(indol-3-yl)-pyridinoimidazole. The chemical structure of the 2-(indol-3-yl)-pyridinoimidazole is represented by formula (I), and R in the formula (I) is a 4-quinolyl group, a 4-isoquinolyl group, a 4-2-methylpyridyl group,
Discovery and Development of 1-[(2-Bromophenyl)sulfonyl]-5-methoxy-3-[(4-methyl-1-piperazinyl)methyl]-1H-indole Dimesylate Monohydrate (SUVN-502): A Novel, Potent, Selective and Orally Active Serotonin 6 (5-HT6) Receptor Antagonist for Potential Treatment of Alzheimer’s Disease
Nirogi, Ramakrishna,Shinde, Anil,Kambhampati, Rama Sastry,Mohammed, Abdul Rasheed,Saraf, Sangram Keshari,Badange, Rajesh kumar,Bandyala, Thrinath Reddy,Bhatta, Venugopalarao,Bojja, Kumar,Reballi, Veena,Subramanian, Ramkumar,Benade, Vijay,Palacharla, Raghava Choudary,Bhyrapuneni, Gopinadh,Jayarajan, Pradeep,Goyal, Vinod,Jasti, Venkat
, p. 1843 - 1859 (2017/03/17)
Optimization of a novel series of 3-(piperazinylmethyl) indole derivatives as 5-hydroxytryptamine-6 receptor (5-HT6R) antagonists resulted in identification of 1-[(2-bromophenyl)sulfonyl]-5-methoxy-3-[(4-methyl-1-piperazinyl)methyl]-1H-indole dimesylate monohydrate (5al, SUVN-502) as a clinical candidate for potential treatment of cognitive disorders. It has high affinity at human 5-HT6R (Ki = 2.04 nM) and selectivity over 100 target sites which include receptors, enzymes, peptides, growth factors, ion channels, steroids, immunological factors, second messengers, and prostaglandins. It has high selectivity over 5-HT2A receptor. It is orally bioavailable and brain penetrant with robust preclinical efficacy. The combination of 5al, donepezil, and memantine (triple combination) produces synergistic effects in extracellular levels of acetylcholine in the ventral hippocampus. Preclinical efficacy in triple combination and high selectivity over 5-HT2A receptors are the differentiating features which culminated in selection of 5al for further development. The Phase-1 evaluation of safety and pharmacokinetics has been completed, allowing for the initiation of a Phase-2 proof of concept study.
Synthesis and bioactivity evaluation of n-arylsulfonylindole analogs bearing a rhodanine moiety as antibacterial agents
Song, Ming-Xia,Li, Song-Hui,Peng, Jiao-Yang,Guo, Ting-Ting,Xu, Wen-Hui,Xiong, Shao-Feng,Deng, Xian-Qing
, (2017/06/28)
Abstract: Due to the rapidly growing bacterial resistance to antibiotics and the scarcity of novel agents under development, bacterial infections are still a pressing global problem, making new types of antibacterial agents, which are effective both alone and in combination with traditional antibiotics, urgently needed. In this paper, seven series of N-arylsulfonylindole analogs 5–11 bearing rhodanine moieties were synthesized, characterized, and evaluated for antibacterial activity. According to the in vitro antimicrobial results, half of the synthesized compounds showed potent inhibition against four Gram-positive bacteria, with MIC values in the range of 0.5–8 μg/mL. For multidrug-resistant strains, compounds 6a and 6c were the most potent, with MIC values of 0.5 μg/mL, having comparable activity to gatifloxacin, moxiflocaxin and norfloxacin and being 128-fold more potent than oxacillin (MIC = 64 μg/mL) and 64-fold more active than penicillin (MIC = 32 μg/mL) against Staphylococcus aureus ATCC 43300.
