305347-19-7

Basic information

• Product Name: 1H-Benzimidazole-2-methanol,1-(1-methylethyl)-(9CI)
• Synonyms: 1H-Benzimidazole-2-methanol,1-(1-methylethyl)-(9CI);(1-isopropyl-1H-benzimidazol-2-yl)methanol(SALTDATA: FREE);(1-Isopropyl-1H-benzoimidazol-2-yl)-methanol;(1-isopropyl-2-benzimidazolyl)methanol;(1-isopropylbenzimidazol-2-yl)methanol;(1-propan-2-ylbenzimidazol-2-yl)methanol;BAS 02937121;IFLab1_001572
• CAS NO: 305347-19-7
• Molecular Formula: C₁₁H₁₄N₂O
• Molecular Weight: 190.245
• Product Categories: BENZIMIDAZOLE
• Mol File: 305347-19-7.mol

Chemical Properties

• Boiling Point: 352.2°C at 760 mmHg
• Flash Point: 166.8°C
• Appearance: /
• Density: 1.16g/cm³
• Vapor Pressure: 1.45E-05mmHg at 25°C
• Refractive Index: 1.595
• PKA: 13.74±0.10(Predicted)
• CAS DataBase Reference: 1H-Benzimidazole-2-methanol,1-(1-methylethyl)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Benzimidazole-2-methanol,1-(1-methylethyl)-(9CI)(305347-19-7)
• EPA Substance Registry System: 1H-Benzimidazole-2-methanol,1-(1-methylethyl)-(9CI)(305347-19-7)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 305347-19-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1H-Benzimidazole-2-methanol,1-(1-methylethyl)-(9CI) is used as a reagent in the synthesis of benzimidazole-thiazolidinedione hybrids. These hybrids exhibit cytotoxic potential and induce apoptosis against selected human cancer cell lines, including prostate, breast, lung, and normal epithelial cells. 1H-Benzimidazole-2-methanol,1-(1-methylethyl)-(9CI) plays a crucial role in the development of novel anticancer agents with improved efficacy and selectivity.

InChI:InChI=1/C11H14N2O/c1-8(2)13-10-6-4-3-5-9(10)12-11(13)7-14/h3-6,8,14H,7H2,1-2H3

Upstream product

• 95-54-5 1,2-diamino-benzene 
• 4856-97-7 2-(Hydroxymethyl)benzimidazole 
• 75-26-3 isopropyl bromide 
• 75-30-9 2-iodo-propane 

Downstream Products

• 339547-40-9 1-isopropyl-1H-benzo[d]imidazole-2-carbaldehyde 

Relevant articles and documents

New (E)-1-alkyl-1H-benzo[d]imidazol-2-yl)methylene)indolin-2-ones: Synthesis, in vitro cytotoxicity evaluation and apoptosis inducing studies

A new series of (E)-benzo[d]imidazol-2-yl)methylene)indolin-2-one derivatives has been synthesized and evaluated for their in vitro cytotoxic activity against a panel of selected human cancer cell lines of prostate (PC-3 and DU-145) and breast (BT-549, MDA-MB-231, MCF-7, 4T1), non-small lung (A549) and gastric (HGC) cancer cells along with normal breast epithelial cells (MCF10A). Among the tested compounds, 8l showed significant cytotoxic activity against MDA-MB-231 and 4T1 cancer cells with IC50values of 3.26 ± 0.24 μM and 5.96 ± 0.67 μM respectively. The compounds 8f, 8i, 8l and 8o were also screened on normal human breast epithelial cells (MCF10A) and found to be safer with lesser cytotoxicity. The treatment of MDA-MB-231 cells with 8l led to inhibition of cell migration ability through disruption of F-actin protein assembly. The flow-cytometry analysis reveals that the cells arrested in G0/G1 phase of the cell cycle. Further, the compound 8l induced apoptosis of MDA-MB-231 cells was characterized by different staining techniques such as Acridine Orange/Ethidium Bromide (AO/EB), DAPI, annexin V-FITC/PI, Rhodamine-123 and MitoSOX red assay. Western blot studies demonstrated that the compound 8l treatment led to activation of caspase-3, increased expression of cleaved PARP, increased expression of pro-apoptotic Bax and decreased expression of anti-apoptotic Bcl-2 in MDA-MB-231 cancer cells.

Synthesis and biological evaluation of new benzimidazole-thiazolidinedione hybrids as potential cytotoxic and apoptosis inducing agents

A series of new benzimidazole-thiazolidinedione hybrids has been synthesized and evaluated for their cytotoxic potential against a selected human cancer cell lines of prostate (PC-3 and DU-145), breast (MDA-MB-231), lung (A549) and a normal breast epithelial cells (MCF10A). Among the tested compounds, 11p exhibited promising cytotoxicity with IC50value of 11.46?±?1.46?μM on A549 lung cancer cell line and did not show significant toxicity on normal MCF10A cells. Lung cancer cells (A549) have been used to know the mechanism of cell growth inhibition and apoptosis inducing effect with compound 11p. The treatment of A549?cells with 11p showed typical apoptotic morphology like cell shrinkage, chromatin condensation and horseshoe shaped nuclei formation. Flow-cytometry analysis revealed the G2/M phase of cell cycle arrest in a dose dependent manner. Preliminary mechanistic studies suggested that the cell migration was inhibited through the disruption of F-actin protein. Acridine orange-ethidium bromide (AO-EB), DAPI, annexin V-FITC/propidium iodide, rhodamine-123 and MitoSOX assays suggested the induction of apoptosis in A549 cells by compound 11p.

Design, synthesis, and biological evaluation of novel thiazolidinediones as PPAR3/FFAR1 dual agonists

Diabetes mellitus is a chronic metabolic disorder that affects more than 180 million people worldwide. Peroxisome proliferator activated receptors (PPARs) are a group of nuclear receptors that have been targeted by the thiazolidinedione (TZD) class of compounds for the management of type II diabetes. PPAR3 is known to regulate adipogenesis and glucose metabolism. Another emerging target for the design of antidiabetic agents is the free fatty acid receptor 1 (FFAR1), previously known as GPR40. Agonists of this receptor were found to enhance insulin secretion in diabetic patients. It has been reported that some thiazolidinediones (TZDs) activate FFAR1 with micromolar potency. In this study, based on docking studies into the crystal structure of PPAR3 and a homology model of FFAR1, nineteen compounds were designed, synthesized, and biologically tested for agonistic activity on both receptors. Nine compounds showed promising dual activity, with two compounds, 11a and 5b, having affinities in the low micromolar range on both targets. These molecules represent the first antidiabetic agents that could act as insulin sensitizers as well as insulin secretagogues.

Structure-Activity Relationship and Pharmacokinetic Studies of 1,5-Diheteroarylpenta-1,4-dien-3-ones: A Class of Promising Curcumin-Based Anticancer Agents

Forty-three 1,5-diheteroaryl-1,4-pentadien-3-ones were designed as potential curcumin mimics, structurally featuring a central five-carbon dienone linker and two identical nitrogen-containing aromatic rings. They were synthesized using a Horner-Wadsworth-Emmons reaction as the critical step and evaluated for their cytotoxicity and antiproliferative activities toward both androgen-insensitive and androgen-sensitive prostate cancer cell lines and an aggressive cervical cancer cell line. Most of the synthesized compounds showed distinctly better in vitro potency than curcumin in the four cancer cell lines. The structure-activity data acquired from the study validated (1E,4E)-1,5-dihereroaryl-1,4-pentadien-3-ones as an excellent scaffold for in-depth development for clinical treatment of prostate and cervical cancers. 1-Alkyl-1H-imidazol-2-yl, ortho pyridyl, 1-alkyl-1H-benzo[d]imidazole-2-yl, 4-bromo-1-methyl-1H-pyrazol-3-yl, thiazol-2-yl, and 2-methyl-4-(trifluoromethyl)thiazol-5-yl were identified as optimal heteroaromatic rings for the promising in vitro potency. (1E,4E)-1,5-Bis(2-methyl-4-(trifluoromethyl)thiazol-5-yl)penta-1,4-dien-3-one, featuring thiazole rings and trifluoromethyl groups, was established as the optimal lead compound because of its good in vitro potency and attractive in vivo pharmacokinetic profiles. (Chemical Equation Presented).