731846-75-6

Usage

InChI:InChI=1/C11H11ClO2/c1-14-11(13)7-6-9-2-4-10(8-12)5-3-9/h2-7H,8H2,1H3/b7-6+

Upstream product

• 5927-18-4 trimethyl phosphonoacetate 
• 73291-09-5 4-chloromethylbenzaldehyde 
• 141286-90-0 methyl (E)-3-(4-(hydroxymethyl)phenyl)acrylate 
• 124-63-0 methanesulfonyl chloride 
• 186581-53-3 diazomethane 
• 1067-74-9 Methyl diethylphosphonoacetate 
• 1642-81-5 p-(chloromethyl)benzoic acid 
• 16473-35-1 4-(hydroxymethyl)benzyl chloride 
• 34040-64-7 p-methyloxycarbonylbenzyl chloride 

Downstream Products

• 950745-60-5 methyl (2E)-3-[4-(iodomethyl)phenyl]-2-propenoate 
• 731846-77-8 C₂₀H₁₈N₂O₂ 
• 441741-65-7 (E)-3-[4-[[[2-(2-methyl-1H-indol-3-yl)ethyl]amino]methyl]phenyl]acrylic acid methyl ester 
• 950745-62-7 (E)-methyl 3-(4-((E)-3,4-dimethoxystyryl)phenyl)acrylate 

Relevant academic research and scientific papers

An improved and efficient synthesis of panobinostat

An improved and efficient method for the synthesis of panobinostat was developed. The commercially available starting material 4-(chloromethyl)benzaldehyde was converted to (E)-methyl 3-[4-(chloromethyl)phenyl]acrylate via the Wittig-Horner reaction and was then directly condensed with 2-(2-methyl-1H-indol-3-yl)ethanamine to afford the key intermediate (E)-methyl 3-[4-({[2-(2-methyl-1H-indol- 3-yl)ethyl]amino}methyl)phenyl]acrylate in a one-pot synthesis reactor. Subsequently a nucleophilic substitution reaction was carried out smoothly to generate the desired compound. The key intermediate and target compound were characterised by HRMS, 1H NMR and 13C NMR. This procedure is operationally simple and would be more suitable for industrial production.

Unravelling the olefin cross metathesis on solid support. Factors affecting the reaction outcome

Olefin cross metathesis on solid support under a variety of conditions is described. A comprehensive analysis considering diverse factors governing the reaction outcome gives a series of patterns for the application of this useful methodology in organic synthesis. If the intrasite reaction is not possible, homodimerization of the soluble olefin is crucial. When the homodimer is less reactive than its monomer, reaction outcome depends on the homodimerization rate, which, in turn, depends on the precatalyst used and the reaction conditions. If the site-site interaction is a feasible process, the cross metathesis product is obtained exclusively when the newly-formed double bond is resilient to further metathetic events. Taking into account these considerations, we have demonstrated that excellent results in terms of cross metathesis coupling can be obtained under the optimized conditions, and that microwave irradiation is also an interesting alternative for the development of a practical and energy-efficient cross metathesis on solid support.

Solid-supported cross metathesis and the role of the homodimerization of the non-immobilized olefin

(Chemical Equation Presented) We have prepared immobilized olefins as models for the cross metathesis using different olefin partners in the presence of second generation Grubbs and Hoveyda-Grubbs precatalysts. We have demonstrated that solid-phase cross metathesis is strongly dependent on the degree of homodimerization of the non-immobilized olefin and the reactivity of such a homodimer. As in the homogeneous phase, the Hoveyda-Grubbs precatalyst was better for immobilized α,β-unsaturated carbonyl compounds.

Design, synthesis, and discovery of stilbene derivatives based on lithospermic acid B as potent protein tyrosine phosphatase 1B inhibitors

Dihydroxy stilbene derivatives were designed based on lithospermic acid B and were prepared from 4-(chloromethyl)benzoic acid. The inhibitory activities of the novel compounds against protein tyrosine phosphatase 1B (PTP1B) were evaluated. 3,4-Dihydroxy stilbene carbonyl compounds (7, 11b, 27b) inhibited PTP1B with IC50 values comparable to molybdate, while the conjugation-extended compound (15b) showed inhibition 3-fold better than preclinical RK682. The introduction of electron withdrawing groups or amides into the second phenyl ring, or extension of the conjugation into the stilbene molecule may increase stability of the generated radicals.

HYDROXAMID ACID DERIVATIVES AS HISTONE DEACETYLASE (HDAC) INHIBITORS

A compound having the following formula (I): wherein R?1? is N-containing heterocyclic ring optionally substituted with one or more suitable substituent(s), R?2? is hydroxyamino, R?3? is hydrogen or a suitable substituent, L?1? is -(CH?2#191)?n#191- (wherein n is an integer of 0 to 6) optionally substituted with one or more suitable substituent(s), wherein one or more methylene(s) may be replaced with suitable heteroatom(s), and L?2? is lower alkenylene, or a salt thereof. The compound is useful as a histone deacetylase inhibitor.

HDAC inhibitor

A compound having the following formula (I): wherein R1 is N-containing heterocyclic ring optionally substituted with one or more suitable substituent(s), R2 is hydroxyamino, R3 is hydrogen or a suitable substituent, L1 is —(CH2)n— (wherein n is an integer of 0 to 6) optionally substituted with one or more suitable substituent(s), wherein one or more methylene(s) may be replaced with suitable heteroatom(s), and L2 is lower alkenylene, or a salt thereof. The compound is useful as a histone deacetylase inhibitor.

GLUTAMIC ACID RECEPTOR AGONIST

A method comprising administering a sulfonamide derivative to a patient requiring activation of glutamate receptors, the sulfonamide derivative represented by the formula STR1 wherein A is a napthyl group, a pyridyl group, a phenyl group, a phenyl group s

Sulfonamide derivatives

A sulfonamide derivative represented by the Formula: STR1 wherein A, B, X, Y, R, m and n are as defined in the specification, and a salt thereof have thromboxane A2 antagonism, therefore they are useful, for example, as blood platelet aggregati