630108-41-7

Basic information

• Product Name: Hydroxylamine, O-[(2,5-dimethoxyphenyl)methyl]- (9CI)
• Synonyms: Hydroxylamine, O-[(2,5-dimethoxyphenyl)methyl]- (9CI)
• CAS NO: 630108-41-7
• Molecular Formula: C₉H₁₃NO₃
• Molecular Weight: 183.20442
• Product Categories: METHOXY
• Mol File: 630108-41-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Hydroxylamine, O-[(2,5-dimethoxyphenyl)methyl]- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Hydroxylamine, O-[(2,5-dimethoxyphenyl)methyl]- (9CI)(630108-41-7)
• EPA Substance Registry System: Hydroxylamine, O-[(2,5-dimethoxyphenyl)methyl]- (9CI)(630108-41-7)

Safety Data

• Hazardous Substances Data: 630108-41-7(Hazardous Substances Data)

Upstream product

• 93-02-7 2,5-dimethoxybenzaldehyde 
• 33524-31-1 2,5-dimethoxybenzyl alcohol 

Downstream Products

• 1446946-12-8 C₁₉H₂₉N₃O₅ 
• 1446946-25-3 7-[3-amino-4-(2',5'-dimethoxybenzyloxyimino)piperidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 
• 1446945-99-8 C₂₀H₂₉N₃O₆ 
• 1446945-86-3 C₂₀H₂₇N₃O₅ 

Relevant articles and documents

IDO inhibitors

Presently provided are methods for (a) modulating an activity of indoleamine 2,3-dioxygenase comprising contacting an indoleamine 2,3-dioxygenase with a modulation effective amount of a compound as described in one of the aspects described herein; (b) treating indoleamine 2,3-dioxygenase (IDO) mediated immunosuppression in a subject in need thereof, comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; (c) treating a medical conditions that benefit from the inhibition of enzymatic activity of indoleamine-2,3-dioxygenase comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; (d) enhancing the effectiveness of an anti-cancer treatment comprising administering an anti-cancer agent and a compound as described in one of the aspects described herein; (e) treating tumor-specific immunosuppression associated with cancer comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; and (f) treating immunosuppression associated with an infectious disease, e.g., HIV-I infection, comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount a compound as described in one of the aspects described herein.

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.

Synthesis, in vitro antimycobacterial and antibacterial evaluation of IMB-070593 derivatives containing a substituted benzyloxime moiety

A series of novel IMB-070593 derivatives containing a substituted benzyloxime moiety and displaying a remarkable improvement in lipophilicity were synthesized and evaluated for their in vitro antimycobacterial and antibacterial activity. Our results reveal that the target compounds 19a-m have considerable Gram-positive activity (MIC: 0.008-32 μg/mL), although they are generally less active than the reference drugs against the Gram-negative strains. In particular, compounds 19h, 19j, 19k and 19m show good activity (MICs: 0.008-4 μg/mL) against all of the tested Gram-positive strains, including ciprofloxacin (CPFX)- and/or levofloxacin (LVFX)-resistant MSSA, MRSA and MSSE. Moreover, compound 19l (MIC: 0.125 μg/mL) is found to be 2-4 fold more active than the parent IMB070593, CPFX and LVFX against M. tuberculosis H37Rv ATCC 27294.

Synthesis of new arylalkoxy amido derivatives as melatoninergic ligands

Amido derivatives 10-18 of the corresponding oxyamines were synthesised as melatoninergic ligands by the reaction of hydroxyphtalimide with the halogeno derivatives or the corresponding alcohols using Mitsunobu reaction conditions. The affinity of the com