18450-28-7Relevant academic research and scientific papers
Design, synthesis, in-vitro evaluation and molecular docking studies of novel indole derivatives as inhibitors of SIRT1 and SIRT2
Manjula, Ramu,Gokhale, Nikhila,Unni, Sruthi,Deshmukh, Prashant,Reddyrajula, Rajkumar,Srinivas Bharath,Dalimba, Udayakumar,Padmanabhan, Balasundaram
, (2019/09/30)
Sirtuins (SIRTs), class III HDAC (Histone deacetylase) family proteins, are associated with cancer, diabetes, and other age-related disorders. SIRT1 and SIRT2 are established therapeutic drug targets by regulating its function either by activators or inhi
Design of C3-Alkenyl-Substituted 2-Indolylmethanols for Catalytic Asymmetric Interrupted Nazarov-Type Cyclization
Wang, Cong-Shuai,Wu, Jia-Le,Li, Can,Li, Lin-Zhi,Mei, Guang-Jian,Shi, Feng
supporting information, p. 846 - 851 (2018/03/06)
The C3-alkenyl-substituted 2-indolylmethanols have been designed as a new class of substrates for catalytic asymmetric interrupted Nazarov-type cyclizations. In the presence of chiral phosphoric acid as a mild chiral Br?nsted acid, the interrupted Nazarov
Design, synthesis, in vitro antiproliferative activity and apoptosis-inducing studies of 1-(3′,4′,5′-trimethoxyphenyl)-3-(2′-alkoxycarbonylindolyl)-2-propen-1-one derivatives obtained by a molecular hybridisation approach
Preti, Delia,Romagnoli, Romeo,Rondanin, Riccardo,Cacciari, Barbara,Hamel, Ernest,Balzarini, Jan,Liekens, Sandra,Schols, Dominique,Estévez-Sarmiento, Francisco,Quintana, José,Estévez, Francisco
, p. 1225 - 1238 (2018/09/04)
Inhibition of microtubule function using tubulin targeting agents has received growing attention in the last several decades. The indole scaffold has been recognized as an important scaffold in the design of novel compounds acting as antimitotic agents. Indole-based chalcones, in which one of the aryl rings was replaced by an indole, have been explored in the last few years for their anticancer potential in different cancer cell lines. Eighteen novel (3′,4′,5′-trimethoxyphenyl)-indolyl-propenone derivatives with general structure 9 were synthesized and evaluated for their antiproliferative activity against a panel of four different human cancer cell lines. The highest IC50 values were obtained against the human promyelocytic leukemia HL-60 cell line. This series of chalcone derivatives was characterized by the presence of a 2-alkoxycarbonyl indole ring as the second aryl system attached at the carbonyl of the 3-position of the 1-(3′,4′,5′-trimethoxyphenyl)-2-propen-1-one framework. The structure–activity relationship (SAR) of the indole-based chalcone derivatives was investigated by varying the position of the methoxy group, by the introduction of different substituents (hydrogen, methyl, ethyl or benzyl) at the N-1 position and by the activity differences between methoxycarbonyl and ethoxycarbonyl moieties at the 2-position of the indole nucleus. The antiproliferative activity data of the novel synthesized compounds revealed that generally N-substituted indole analogues exhibited considerably reduced potency as compared with their parent N-unsubstituted counterparts, demonstrating that the presence of a hydrogen on the indole nitrogen plays a decisive role in increasing antiproliferative activity. The results also revealed that the position of the methoxy group on the indole ring is a critical determinant of biological activity. Among the synthesized derivatives, compound 9e, containing the 2-methoxycarbonyl-6-methoxy-N-1H-indole moiety exhibited the highest antiproliferative activity, with IC50 values of 0.37, 0.16 and 0.17 μM against HeLa, HT29 and MCF-7 cancer cell lines, respectively, and with considerably lower activity against HL-60 cells (IC50: 18 μM). This derivative also displayed cytotoxic properties (IC50 values ～1 μM) in the human myeloid leukemia U-937 cell line overexpressing human Bcl-2 (U-937/Bcl-2) via cell cycle progression arrest at the G2-M phase and induction of apoptosis. The results obtained also demonstrated that the antiproliferative activity of this molecule is related to inhibition of tubulin polymerisation. The presence of a methoxy group at the C5- or C6-position of the indole nucleus, as well as the absence of substituents at the N-1-indole position, contributed to the optimal activity of the indole-propenone-3′,4′,5′-trimethoxyphenyl scaffold.
Novel Indole-Quinazolinone Based Amides as Cytotoxic Agents
Gokhale, Nikhila,Panathur, Naveen,Dalimba, Udayakumar,Nayak, Pawan G.,Pai, K. Sreedhar Ranganath
, p. 513 - 524 (2016/04/19)
Indole-quinazolinone hybrids with active amides were synthesized, characterized, and assessed for their cytotoxicity. Two molecules displayed substantial activity in sulphorhodamine B assay method.
Lateral lithiation-initiated annulations in the synthesis of 1-oxygenated carbazole alkaloids and a cycloheptacarbazole
Jana, Amit,Pahari, Pallab,Mal, Dipakranjan
supporting information; scheme or table, p. 1769 - 1774 (2012/08/29)
Anionic [4+2] annulation of lithiated furoindolones with dimethyl maleate followed by selective demethoxycarbonylation provides an efficient synthetic route to 3-methoxycarbonylcarbazoles. The route has led to the straightforward synthesis of two natural
Indole-olefin-oxazoline (IndOlefOx)-ligands: Synthesis and utilization in asymmetric Rh-catalyzed conjugate addition
Kuuloja, Noora,Tois, Jan,Franzen, Robert
experimental part, p. 468 - 475 (2011/05/19)
The synthesis and utility of novel indole-olefin-oxazoline (IndOlefOx)-ligands are described. The use of these ligands was demonstrated in rhodium catalyzed asymmetric conjugate additions between 2-cyclopentenone, 2-cyclohexenone, and 2-cycloheptenone with different boron reagents with good yields and enantioselectivities of up to 94%.
Indoles and pyridazinoindoles as nonnucleoside analog inhibitors of HIV-1 reverse transcriptase
Font, M.,Monge, A.,Cuartero, A.,Ellorriaga, A.,Martinez-Irujo, J.J.,et al.
, p. 963 - 972 (2007/10/03)
The synthesis and the study of the activity of new indol-2-carboxamides and pyridazinoindoles as inhibitors of HIV-1 reverse transcriptase (RT) are presented.The activity of the compounds synthesized as inhibitors of different types of HIV-1 RT (wild type enzyme and mutant forms P236L, Y181C and P236L/Y181C) was evaluated.The activity of the most active compounds was investigated in the syncytia reduction in vitro assay, in HIV-1IIIB-infected HT4lacZ-1 cells.Their potential cytotoxicity was determined in parallel.Two lead compounds,N-piperazin>-5,6-methylenedioxy indol-2-carboxamide 7q and N-piperazin>-5,6-methylenedioxyindol-2-carboxamide 7s have been identified. - Keywords: indole; nonnucleoside RT inhibitor; syncytia assay; HIV-1IIIBHT4lacZ-1 cells
Abnormal Fischer indolization and its related compounds. XXII. Fischer indolization of ethyl pyruvate 2-(2-chloro- and 2,6-dichlorophenyl)methylhydrazones
Ishii,Murakami,Ishikawa
, p. 597 - 604 (2007/10/02)
The Fischer indolization of ethyl pyruvate 2-(2-chlorophenyl)methylhydrazone (17) with HCI/EtOH proceeded rapidly to give six 1-methylindoles, ethyl 7-chloro (19), 6-chloro (22), and unsubstituted (24)-1-methylindole-2-carboxylates, and dichloro derivativ
