56559-62-7

Basic information

• Product Name: 1-METHYL-1H-INDOLE-3-CARBOHYDRAZIDE
• Synonyms: 1-methyl-1H-indole-3-carbohydrazide(SALTDATA: FREE)
• CAS NO: 56559-62-7
• Molecular Formula: C₁₀H₁₁N₃O
• Molecular Weight: 189.2187
• Mol File: 56559-62-7.mol
• Article Data: 11

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.3g/cm³
• Refractive Index: 1.652
• CAS DataBase Reference: 1-METHYL-1H-INDOLE-3-CARBOHYDRAZIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-METHYL-1H-INDOLE-3-CARBOHYDRAZIDE(56559-62-7)
• EPA Substance Registry System: 1-METHYL-1H-INDOLE-3-CARBOHYDRAZIDE(56559-62-7)

Safety Data

• Hazardous Substances Data: 56559-62-7(Hazardous Substances Data)

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

• 603-76-9 1-methylindole 
• 487-89-8 Indole-3-carboxaldehyde 
• 942-24-5 3-methoxycarbonylindole 
• 108438-43-3 methyl 1-methyl-1H-indole-3-carboxylate 
• 120-72-9 indole 
• 771-50-6 1H-indole-3-carboxylic acid 
• 776-41-0 indole-3-carboxylic acid ethyl ester 
• 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 
• 56559-60-5 ethyl 1-methyl-1H-indole-3-carboxylate 

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 articles and documents

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.

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, 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.