17630-75-0Relevant academic research and scientific papers
Attempted synthesis of a Tenidap isomer and formation of an unexpected stable water adduct
Esses-Reiter,Reiter
, p. 927 - 933 (2000)
An attempt to synthesize the Tenidap isomer 13 was performed starting from 2-ethoxy-5-chloroindole (9). The acylation and carbamoylation reactions of 9 led to the expected intermediate 12, however the hydrolysis of 12 in acidic or alkaline media did not y
Synthesis of novel 3-(benzothiazol-2-ylmethylene)indolin-2-ones
Zhang, Chao,Xu, Juan,Zhao, Xinyu,Kang, Congmin
, p. 537 - 540 (2017)
A mild method for the synthesis of 3-(benzothiazol-2-ylmethylene)indolin-2-ones via the aldol condensation of substituted indolin-2-ones and benzothiazole-2-carbaldehyde is described. This new procedure has significant advantages, such as mild conditions, high yields and simple work-up.
Synthesis of indolones and quinolones by reductive cyclisation of o-nitroaryl acids using zinc dust and ammonium formate
Dinesh, Bhima Reddy,Baba, A. Ramesha,Sankar, K. Udaya,Gowda, D. Channe
, p. 287 - 288 (2008)
A novel protocol for the synthesis of indolone and quinolone derivatives from o-nitroaryl acids was developed using Zn and HCO2NH4 under supercritical fluid carbon dioxide (scCO2) medium. The process involves the reduction of the nitro group to an amino group followed by in situ cyclisation.
Ultrasound promoted clay catalyzed efficient and one pot synthesis of substituted oxindoles
Dandia,Bhati,Jain,Sharma
, p. 1143 - 1147 (2011)
A simple facile, one-pot synthesis of oxindoles in reasonable purity is reported via intramolecular Friedal-Craft cyclization. Clay KSF is an inexpensive, efficient and mild catalyst for the synthesis of substituted oxindoles by the reaction of chloroacetyl chloride and various anilines under the influence of ultrasonic irradiation under solvent-free conditions. The remarkable advantages of this method are the simple experimental procedures, short reaction times, high yields of products, suitability for a wide variety of substituents, and the green aspects through the avoidance of toxic catalyst and solvents.
Direct Superacid-Promoted Difluoroethylation of Aromatics
Artault, Maxime,Vitse, Kassandra,Martin-Mingot, Agnès,Thibaudeau, Sébastien
supporting information, (2021/12/22)
Under superacid conditions, aromatic amines are directly and regioselectively 1,1-difluoroethylated. Low temperature in situ NMR studies confirmed the presence of benzylic α-fluoronium and α-chloronium ions as key intermediates in the reaction. This method has a wide substrate scope and can be applied to the late-stage functionalization of natural alkaloids and active pharmaceutical ingredients.
A novel methodology for the efficient synthesis of 3-monohalooxindoles by acidolysis of 3-phosphate-substituted oxindoles with haloid acids
Liu, Li,Li, Yue,Huang, Tiao,Kong, Dulin,Wu, Mingshu
, p. 2321 - 2328 (2021/09/22)
A novel method for the synthesis of 3-monohalooxindoles by acidolysis of isatin-derived 3-phosphate-substituted oxindoles with haloid acids was developed. This synthetic strategy involved the preparation of 3-phosphate-substituted oxindole intermediates and SN1 reactions with haloid acids. This new procedure features mild reaction conditions, simple operation, good yield, readily available and inexpensive starting materials, and gram-scalability.
Room Temperature Benzofused Lactam Synthesis Enabled by Cobalt(III)-Catalyzed C(sp2)?H Amidation
Tian, Xun,Li, Xin,Duan, Shengzu,Du, Ya,Liu, Tongqi,Fang, Yongsheng,Chen, Wen,Zhang, Hongbin,Li, Minyan,Yang, Xiaodong
, p. 1050 - 1058 (2020/12/18)
Benzofused lactams, especially indolin-2-one and dihydroquinolin-2-one are popular structural motives in durgs and natural products. Herein, we developed a room temperature and robust synthesis of benzofused lactams through cobalt(III)-catalyzed C(sp
Design and Synthesis of DNA-Interactive β-Carboline–Oxindole Hybrids as Cytotoxic and Apoptosis-Inducing Agents
Tokala, Ramya,Thatikonda, Sowjanya,Vanteddu, Usha Sree,Sana, Sravani,Godugu, Chandraiah,Shankaraiah, Nagula
, p. 1909 - 1922 (2018/09/14)
A new series of (E)-3-[(1-aryl-9H-pyrido[3,4-b]indol-3-yl)methylene]indolin-2-one hybrids were synthesized and evaluated for their in vitro cytotoxic activity against a panel of selected human cancer cell lines, namely, HCT-15, HCT-116, A549, NCI-H460, and MCF-7, including HFL. Among the tested compounds, (E)-1-benzyl-5-bromo-3-{[1-(2,5-dimethoxyphenyl)-9H-pyrido[3,4-b]indol-3-yl]methylene}indolin-2-one (10 s) showed potent cytotoxicity against HCT-15 cancer cells with an IC50 value of 1.43±0.26 μm and a GI50 value of 0.89±0.06 μm. Notably, induction of apoptosis by 10 s on the HCT-15 cell line was characterized by using different staining techniques, such as acridine orange/ethidium bromide (AO/EB) and DAPI. Further, to understand the mechanism of anticancer effects, various assays such as annexin V-FITC/PI, DCFDA, and JC-1were performed. The flow cytometric analysis revealed that compound 10 s arrests the HCT-15 cancer cells at the G0/G1 phase of the cell cycle. Additionally, western blot analysis indicated that treatment of 10 s on HCT-15 cancer cells led to decreased expression of anti-apoptotic Bcl-2 and increased protein expression of both pro-apoptotic Bax and caspase-3, -8, and -9, and cleaved PARP with reference to actin. Next, a clonogenic assay revealed the inhibition of colony formation in HCT-15 cancer cells by 10 s in a dose-dependent manner. Moreover, upon testing on normal human lung cells (HFL), the compounds were observed to be safer with a low toxicity profile. In addition, viscosity and molecular-docking studies showed that compound 10 s has typical intercalation with DNA.
Synthesis of 2-Oxindoles from Substituted Indoles by Hypervalent-Iodine Oxidation
Jiang, Xinpeng,Zheng, Cong,Lei, Lijun,Lin, Kai,Yu, Chuanming
, p. 1437 - 1442 (2018/04/06)
A practical conversion of indoles into the corresponding 2-oxindoles is achieved efficiently using a hypervalent iodine reagent. This oxidation is amenable to different substituted indoles, and allows the synthesis of a wide range of synthetically valuable substituted 2-oxindoles in up to 90 % yield. Furthermore, Ropinirole, a drug used to alleviate the symptoms of Parkinson's disease, was synthesized in three steps in an overall yield of 44 % using this method.
Selective formation of γ-lactams via C-H amidation enabled by tailored iridium catalysts
Hong, Seung Youn,Park, Yoonsu,Hwang, Yeongyu,Kim, Yeong Bum,Baik, Mu-Hyun,Chang, Sukbok
, p. 1016 - 1021 (2018/03/09)
Intramolecular insertion of met al nitrenes into carbon-hydrogen bonds to form γ-lactam rings has traditionally been hindered by competing isocyanate formation. We report the application of theory and mechanism studies to optimize a class of pentamethylcyclopentadienyl iridium(III) catalysts for suppression of this competing pathway. Modulation of the stereoelectronic properties of the auxiliary bidentate ligands to be more electron-donating was suggested by density functional theory calculations to lower the C-H insertion barrier favoring the desired reaction. These catalysts transform a wide range of 1,4,2-dioxazol-5-ones, carbonylnitrene precursors easily accessible from carboxylic acids, into the corresponding γ-lactams via sp3 and sp2 C-H amidation with exceptional selectivity. The power of this method was further demonstrated by the successful late-stage functionalization of amino acid derivatives and other bioactive molecules.
