1885-53-6

Basic information

• Product Name: 2-(biphenyl-4-ylmethoxy)-1H-isoindole-1,3(2H)-dione
• CAS NO: 1885-53-6
• Molecular Formula: C₂₁H₁₅NO₃
• Molecular Weight: 329.3487
• Mol File: 1885-53-6.mol

Chemical Properties

• Boiling Point: 516.6°C at 760 mmHg
• Flash Point: 266.2°C
• Density: 1.33g/cm³
• Vapor Pressure: 8.85E-11mmHg at 25°C
• Refractive Index: 1.688
• CAS DataBase Reference: 2-(biphenyl-4-ylmethoxy)-1H-isoindole-1,3(2H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(biphenyl-4-ylmethoxy)-1H-isoindole-1,3(2H)-dione(1885-53-6)
• EPA Substance Registry System: 2-(biphenyl-4-ylmethoxy)-1H-isoindole-1,3(2H)-dione(1885-53-6)

Safety Data

• Hazardous Substances Data: 1885-53-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-(biphenyl-4-ylmethoxy)-1H-isoindole-1,3(2H)-dione is used as a potential anti-cancer agent for its ability to inhibit VEGFR-2 phosphorylation and downstream signaling pathways, which are critical for tumor angiogenesis and progression. This makes it a candidate for the development of new cancer therapies.
Used in Cancer Research:
In the field of cancer research, 2-(biphenyl-4-ylmethoxy)-1H-isoindole-1,3(2H)-dione is used as a research tool to study the mechanisms of angiogenesis and tumor growth, providing insights into the development of targeted therapies for cancer treatment.

Upstream product

• 3218-36-8 4-Phenylbenzaldehyde 
• 524-38-9 N-hydroxyphthalimide 
• 3597-91-9 biphenyl-4-yl methanol 

Downstream Products

• 139259-72-6 p-phenylbenzyl benzohydroxamate 
• 681146-20-3 2-[2-(biphenyl-4-ylmethoxyamino)-ethyl]-isoindole-1,3-dione 

Relevant articles and documents

Toward the rational development of peptidomimetic analogs of the C-terminal endothelin hexapeptide: Development of a theoretical model

In an early report on the structure-activity relationship of endothelin (ET) peptides, it was reported that the C-terminal hexapeptide ET(16-21), His-Leu-Asp-Ile-Ile-Trp, is the minimum ET fragment which maintains biological activity in some, but not all

Rh(III)-Catalyzed C-H Amidation of Arenes with N-Methoxyamide as an Amidating Reagent

The Rh(III)-catalyzed amidation of C(sp2)-H bonds has been reported by employing the N-methoxyamide as a novel amino source. An excellent level of functional group tolerance can be achieved when N-methoxyamide derivatives are used as the amidating reagents. Importantly, several known bioactive compounds such as Aminalon, Pregabalin, Gabapentin, and Probenecid can be transformed to effective amidating reagents, as a way to facilitate the development of new bioactive molecules.

O-alkylhydroxylamines as rationally-designed mechanism-based inhibitors of indoleamine 2,3-dioxygenase-1

Indoleamine 2,3-dioxygenase-1 (IDO1) is a promising therapeutic target for the treatment of cancer, chronic viral infections, and other diseases characterized by pathological immune suppression. Recently important advances have been made in understanding IDO1's catalytic mechanism. Although much remains to be discovered, there is strong evidence that the mechanism proceeds through a heme-iron bound alkylperoxy transition or intermediate state. Accordingly, we explored stable structural mimics of the alkylperoxy species and provide evidence that such structures do mimic the alkylperoxy transition or intermediate state. We discovered that O-benzylhydroxylamine, a commercially available compound, is a potent sub-micromolar inhibitor of IDO1. Structure-activity studies of over forty derivatives of O-benzylhydroxylamine led to further improvement in inhibitor potency, particularly with the addition of halogen atoms to the meta position of the aromatic ring. The most potent derivatives and the lead, O-benzylhydroxylamine, have high ligand efficiency values, which are considered an important criterion for successful drug development. Notably, two of the most potent compounds demonstrated nanomolar-level cell-based potency and limited toxicity. The combination of the simplicity of the structures of these compounds and their excellent cellular activity makes them quite attractive for biological exploration of IDO1 function and antitumor therapeutic applications.

A solid-phase approach to DDB derivatives

Since the discovery of 2,2′-dimethoxycarbonyl-4,4-dimethoxy-5,6, 5′,6′-biomethylenedioxy-biphenyl (DDB) as a potent anti-HBV agent, we have studied the structure-activity relationships of 4,4′-dimethoxy-5, 6,5′,6′-dimethenedioxy-2-alkyloxycarbonyl-2′-(4-substituted benzyl piperazin-1-yl)carbonyl-biphenyl as anti-HBV agents. Therefore, it is rational to extend this study to the 3,3′-disustituted-4,4′- dimethoxy-5,6,5′,6′-dimethenedioxy-2-alkyloxycarbonyl-2′- Serine derivatives. Thus, in an attempt to develop an efficient method for the preparation of a large number of DDB derivatives, the reaction between a DDB acid chloride and serine derivatives on solid support was studied. The structure of resulted compounds was confirmed by LC-MS and 1H NMR analysis. Compounds 2a, 2d, 2f, 2j showed in vitro anti-HBV activity without significant toxicity up to 100 μM.

1-Benzyloxy-4,5-dihydro-1H-imidazol-2-yl-amines, a novel class of NR1/2B subtype selective NMDA receptor antagonists

Screening of the Roche compound depository led to the identification of (1-benzyloxy-4,5-dihydro-1H-imidazol-2-yl)-butyl amine 4, a structurally novel NR1/2B subtype selective NMDA receptor antagonist. The structure-activity relationships developed in this series resulted in the discovery of a novel class of potent and selective NMDA receptor blockers displaying activity in vivo.