56559-62-7

Usage

Carbohydrazide derivative

A compound derived from carbohydrazide, which is a chemical structure containing a nitrogen atom double-bonded to two hydroxyl groups.

Methyl group attachment

A methyl group (CH3) is attached to the 1-position of the indole ring, which influences the compound's properties and reactivity.

Indole ring

A part of the compound's structure, consisting of a six-membered aromatic ring with a nitrogen atom at one end.

Potential applications in organic synthesis

The compound can be used as a building block or reagent in the synthesis of more complex organic molecules.

Potential applications in medicinal chemistry

The compound may be used to develop new drugs or therapies due to its ability to form stable complexes with transition metals.

Ability to form stable complexes with transition metals

The compound can bind to transition metals, which may enhance its pharmacological properties and potential applications.

Investigated for anticancer properties

Researchers have explored the compound's potential to inhibit cancer cell growth and proliferation.

Investigated for antiviral properties

The compound has been studied for its potential to inhibit viral replication and infection.

Versatile and valuable chemical compound

Due to its diverse properties and potential applications, 1-METHYL-1H-INDOLE-3-CARBOHYDRAZIDE is considered a valuable compound in various fields.

InChI:InChI=1/C10H11N3O/c1-13-6-8(10(14)12-11)7-4-2-3-5-9(7)13/h2-6H,11H2,1H3,(H,12,14)

Upstream product

• 56559-60-5 ethyl 1-methyl-1H-indole-3-carboxylate 
• 120-72-9 indole 
• 108438-43-3 methyl 1-methyl-1H-indole-3-carboxylate 
• 942-24-5 3-methoxycarbonylindole 
• 487-89-8 Indole-3-carboxaldehyde 
• 32387-21-6 1-methyl-3-indolecarboxylic acid 
• 151621-88-4 2,2,2-trichloro-1-(1-methyl-1H-indol-3-yl)ethan-1-one 
• 603-76-9 1-methylindole 
• 771-50-6 1H-indole-3-carboxylic acid 
• 776-41-0 indole-3-carboxylic acid ethyl ester 

Downstream Products

• 1354714-54-7 C₂₆H₂₀ClFN₄O 
• 1354714-55-8 C₂₇H₂₃ClN₄O₂ 
• 1354714-53-6 C₂₇H₂₃FN₄O₂ 
• 891608-70-1 C₁₇H₁₅ClN₄OS 
• 894231-51-7 C₁₇H₁₆N₄OS 
• 1396743-74-0 C₁₇H₁₄N₄S 

Relevant academic research and scientific papers

Discovery of novel indole-1,2,4-triazole derivatives as tubulin polymerization inhibitors

A series of novel indole-1,2,4-triazole derivatives have been designed, synthesized, and evaluated as potential tubulin polymerization inhibitors. The top hit 12, bearing the 3,4,5-trimethoxyphenyl moiety, exhibited substantial anti-proliferative activity against HepG2, HeLa, MCF-7, and A549 cells in vitro with IC50 values of 0.23 ± 0.08 μM, 0.15 ± 0.18 μM, 0.38 ± 0.12 μM, and 0.30 ± 0.13 μM, respectively. It also inhibited tubulin polymerization with the IC50 value of 2.1 ± 0.12 μM, which was comparable with that of the positive controls. Furthermore, compound 12 regulated the expression of cell cycle-related proteins (Cyclin B1, Cdc25c, and Cdc2) and apoptosis-related proteins (Bcl-2, Bcl-x, and Mcl-1). Mechanistically, compound 12 could arrest cell cycle at the G2/M phase, thus induce an increase of apoptotic cell death. In addition, molecular docking hinted the possible interaction mode of compound 12 into the colchicine binding site of tubulin heterodimers. According to the applications of microtubule-targeting agents in both direct and synergistic cancer therapies, we hope this work might be of significance for future researches.

Synthesis, anticancer evaluation and molecular docking studies of 2,5-bis(indolyl)-1,3,4-oxadiazoles, Nortopsentin analogues

A series of ten novel 2,5-bis(indolyl)-1,3,4-oxadiazoles were designed and synthesized. All these compounds were evaluated for their cytotoxicity against four cancer cell lines namely A549, MDA-MB-231, MCF-7 and HeLa using MTT reduced assay. Among them, compound 12e exhibited good cytotoxicity on MCF-7 cell line with IC50 value of 1.8 μM and it was identified as a promising drug lead when compared to the standard drug doxorubicin (IC50 value 0.98 μM). Compound, 12h exhibited better antitumor activity against three cancer cell lines i.e., lung (A549), breast (MCF-7) and cervical (HeLa) with IC50 values of 3.3 μM, 2.6 μM and 6.34 μM respectively. The impact of these compounds on colchicine binding site of tubulin polymer was carefully investigated using molecular docking studies and interpretations between actives and inactive were explained.

Discovery of new indole-based 1,2,4-triazole derivatives as potent tubulin polymerization inhibitors with anticancer activity

Thirty-six novel indole-based 1,2,4-triazole derivatives were designed and synthesized through the molecular hybrid strategy. The bioassay results revealed that 9p displayed excellent antiproliferative efficacies in the nanomolar range against HeLa cells. Importantly, the compound exhibited no obvious cytotoxic activity (IC50 > 100 μM) toward HEK-293, a normal human embryonic kidney cell line. Mechanism analysis indicated that 9p significantly arrested the cell cycle at the G2/M phase and induced apoptosis in HeLa cells in a dose-dependent manner. Further evidence demonstrated that the promising compound effectively inhibited tubulin polymerization with an IC50 value of 8.3 μM, and molecular docking studies revealed that 9p well occupied the colchicine-site in tubulin. The present study highlights that indole-triazole hybrids might be used as a promising scaffold to develop novel tubulin polymerization inhibitors for cancer treatment.

Synthesis, antiproliferative and apoptosis induction potential activities of novel bis(indolyl)hydrazide-hydrazone derivatives

In recent years, indole-indazolyl hydrazide-hydrazone derivatives with strong cell growth inhibition and apoptosis induction characteristics are being strongly screened for their cancer chemo-preventive potential. In the present study, N-methyl and N,N-dimethyl bis(indolyl)hydrazide-hydrazone analog derivatives were designed, synthesized and allowed to evaluate for their anti-proliferative and apoptosis induction potential against cervical (HeLa), breast (MCF-7 and MDA-MB-231) and lung (A549) cancer cell lines relative to normal HEK293 cells. The MTT assay in conjunction with mitochondrial potential assays and the trypan blue dye exclusion were employed to ascertain the effects of the derivatives on the cancer cells. Further, mechanistic studies were conducted on compound 14a to understand the biochemical mechanisms and functional interactions with various signaling pathways triggered in HeLa and MCF-7 cells. Compound 14a induced apoptosis via caspase independent pathway through the participation of mitogen-activated protein kinases (MAPK) such as extracellular signal related kinase (ERK) and p38 as well as p53 pathways. It originates the activation of pro-apoptotic proteins such as Bak and Mcl-1s and also strongly induced the generation of reactive oxygen species. In downstream signaling pathway, activated p53 protein interacted with MAPK pathways, including SAPK/c-Jun N-terminal protein kinase (JNK), p38 and ERK kinases resulting in apoptotic cell death. The involvement of MAPK cascades such as p38, ERK and p38 on compound 14a induced apoptotic cell death was evidenced by the fact that the inclusion of specific inhibitors of p38, ERK1/2 and JNK MAPK (SB2035809, PD98059 and SP600125) prevented the compound 14a towards induced apoptosis. The results clearly showed that MAP kinase cascades were crucial for apoptotic response in compound 14a induced cellular killing and were dependent on p53 activity. Based on the results, compound 14a was identified as a promising candidate for cancer therapeutics and these findings furnish a basis for further in vivo experiments on anti-proliferative activity.

Synthesis, anticancer evaluation and molecular docking studies of bis(indolyl) triazinones, Nortopsentin analogs

Abstract: A new series of bis indolyl tri keto diazo compounds and 3,5-bis(3′-indolyl) triazinones were designed and synthesized as anticancer agents. Their anticancer activity was screened in vitro towards four different human cancer cell lines like HeLa, MCF-7, MDA-MB-231 and A549 cell lines. Among them, compounds 17a and 17b showed potent cytotoxicity with inhibition (IC50) values of 4.6 and 1.3?μM on Human Cervical cancer cell line, respectively. The in silico simulation studies using ADT 1.5.6 tools revealed unique interactions of indole ring of compound 17b with colchicines active site residue Tyr312 could be a valid reason behind its maximum potency when compared to remaining compounds in responsible of its higher activity.

Derivatives containing 1,2,4-triazole framework and preparation method and application thereof

The invention discloses derivatives containing a 1,2,4-triazole framework and a preparation method and application thereof. The structural formula of the derivatives containing formula 1,2,4-triazole framework is as shown in the specification, where R1 is selected from -H, -F, -Cl and -Br; R2 is selected from -H, -OCH3, -Cl, -Br and -F; R3 is selected from -H, -OCH3, -Cl, -Br, -F, -CH3, -I and -CF3; R4 is selected from -H and -OCH3; and R5 is selected from -H and -F. The synthetic method disclosed by the invention is simple in process, involves few steps, is relatively low in cost, efficient and simple, has good universality and can be produced in batches.

Synthesis and functionalization of some new pyridazino[4,5-b]indole derivatives

Starting from the indole-fused pyridazinone 5, a series of new pyridazino[4,5-b]indoles o potential pharmaceutical interest (9-18), was prepared. Compounds 20 and 21 were obtained b nucleophilic displacement of the chlorine atom of 19. Thionation of the chloro derivative 19 gav the thione compound 23, while its reaction with sodium azide gave a tetracyclic system, namel the tetrazolopyridazinoindole 22. Dehalogenation of the chloro compound 19 gave a 3-Az analogue of the natural product, Harman.

A series of 2-arylamino-5-(indolyl)-1,3,4-thiadiazoles as potent cytotoxic agents

A series of 2-arylamino-5-(indolyl)-1,3,4-thiadiazoles 6a-v were prepared and studied for their anticancer activity against selected human cancer cell lines. The reaction of indolylhydrazides 3a-h with a variety of aryl isothiocyanates 4 afforded the key intermediate thiosemicarbazides 5a-v, which upon treatment with acetyl chloride produced the 2-arylamino-5-(indolyl)-1,3,4- thiadiazoles 6a-v in good yields. Most of the synthesized compounds showed selective cytotoxicity towards human breast cancer cell line (MDA-MB-231). Of the synthesized 2-arylamino-5-(indolyl)-1,3,4-thiadiazoles, compound 6f is the most potent towards tested cancer cell lines (IC50 = 0.15-1.18 μM).

Novel bis(indolyl)hydrazide-hydrazones as potent cytotoxic agents

A series of bis(indolyl) hydrazide-hydrazones 5a-n were synthesized and evaluated for their cytotoxicity against selected human cancer cell lines. The reaction of indole-3-carboxaldehyde 2 with indole-3-carbohydrazide 4 in presence of catalytic amount of acetic acid afforded 5a-n in good yields. Among the synthesized bis(indolyl)hydrazide-hydrazones, the compound 5b with N-(p-chlorobenzyl) and bromo substituents was found to be the most potent against multiple cancer cell lines (IC50 = 1.0 μM, MDA-MB-231). The compound 5k exhibited selective cytotoxicity against breast cancer cell line MCF7 (IC50 = 3.1 μM).