40614-20-8

Upstream product

• 108-95-2 phenol 
• 924-50-5 Methyl 3,3-dimethylacrylate 
• 638-10-8 ethyl 3-methylbut-2-enoate 
• 54897-52-8 phenyl 3,3-dimethylacrylate 
• 29598-22-9 4,4-dimethyl-2-oxo-chroman 
• 3350-78-5 3,3-Dimethylacryloyl chloride 

Downstream Products

• 129967-37-9 3-(2'-(Benzyloxy)phenyl)-3,3-dimethylpropanol 
• 121374-67-2 3-<2-O-(methoxymethyl)-2-hydroxyphenyl>-3,3-dimethyl-1-propanol 
• 81246-49-3 3-<2-((methylthio)methoxy)phenyl>-3,3-dimethyl-1-propanol 

Relevant academic research and scientific papers

CHROMAN-SUBSTITUTED, TETRAHYDROQUINOLINE-SUBSTITUTED AND THIOCHROMAN-SUBSTITUTED HETEROAROTINOIDS AS ANTI-CANCER AGENTS

Chemical compounds that inhibit cancer cell growth are provided. The compounds are heteroarotinoids and derivatives thereof with oxygen, nitrogen or sulfur in chroman systems, tetrahydroquinoline systems, and tetrahydrothiochroman systems.

COMPOUNDS AND COMPOSITIONS FOR OCULAR DELIVERY

The present invention provides new prodrags of Sunitinib, Brinzolamide, and Dorzolamide and compositions to treat medical disorders, for example glaucoma, a disorder or abnormality related to an increase in intraocular pressure (TOP), a disorder requiring neuroprotection, age-related macular degeneration, or diabetic retinopathy.

Design, Synthesis, and Cellular Uptake of Oligonucleotides Bearing Glutathione-Labile Protecting Groups

Glutathione-labile protecting groups for phosphodiester moieties in oligonucleotides were designed, synthesized, and incorporated into oligonucleotides. The protecting groups on the phosphodiester moieties were cleaved in a buffer containing 10 mM glutath

Activity of oxygen-versus sulfur-containing analogs of the Flex-Het anticancer agent SHetA2

Five series of chromans with urea and thiourea linkers connecting a chroman unit (ring A) and a 4-substituted benzene unit (ring B) have been prepared and evaluated relative to SHetA2 (NSC 721689) for activity against the human A2780 ovarian cancer cell l

HYDROGEN SULFIDE PRECURSORS AND CONJUGATES THEREOF

The present invention provides methods of forming hydrogen sulfide. The methods include contacting a precursor compound with an unmasking agent; wherein the precursor compound comprises a hydrogen sulfide releasing moiety and a masked nucleophile; and wherein the contacting is conducted under conditions sufficient for cyclization of the precursor compound via lactone or lactam formation; thereby releasing hydrogen sulfide from the precursor compound. Hydrogen sulfide precursor compounds according to Formula (I) are also described, as well as methods for treating diseases and conditions using hydrogen sulfide precursors.

The Lactonization of 2'-Hydroxyhydrocinnamic Acid Amides: A Potential Prodrug for Amines

The lactoniaztion of two hydroxy amides - 4-methoxyaniline 3-(2'-hydroxyphenyl)-3,3-dimethylpropionic acid amide (2b) and 4-methoxyaniline 3-(2'-hydroxy-4',6'-dimethylphenyl)-3,3-dimethylpropionic acid amide (3b) - was studied over a pH range of 1-8.Due to the slowness of its reaction, a third hydroxy amide - 4-methoxyaniline 3-(2'-hydroxyphenyl)propionic acid amide (1b) - was investigated only at pH values of 7.5 and 10.The lactonization of 2b and 3b, which was found to be subject to general catalysis by buffer components, was observed to be catalyzed concurrently but not concertedly by both the acidic and basic forms of the buffer.The buffer-independent pH rate profiles for the lactonization of 2b and 3b were found to obey the equation k0 = kH++> + kH2O + kOH-->, indicating that the reaction is also subject to specific catalysis by hydronium and hydroxide ions.A Broenstedt analysis of the rate constants for buffer catalysis gave α and β values of 0.30 +/- 0.02 and 0.54 +/- 0.04, respectively, for 3b.The rate constants for the accelerated lactonization of 1b at 50, 70, and 90 deg C and pH 10 were used to calculate values of 14.7 +/- 0.8 kcal/mol and -9.5 +/- 2.3 eu for the activation parameters, ΔH(excit.) and ΔS(excit.), respectively.Comparison of the observed rates of lactonization at pH 7.5 and 30 deg C for the three hydroxy amides allowed an estimate of the extent of rate enhancement provided by addition of a partial or total "trimethyl lock" for the hydroxy amide lactonization reaction under near physiological conditions.The order of reactivity of the three hydroxy amides was found to be 3b >> 2b > 1b with rate enhancement factors of 2.5E4, 44, and 1, respectively.This study was begun with the objective of generating a hydroxy amide of very high reactivity at physiological pH for development into amine prodrug forms. 3b, which exhibited a half-life of 65 s at pH 7.5, has been chosen for further development as an amine prodrug.

Conformationally Restricted Retinoids

A series of conformationally restricted retinoids was synthesized and screened in two assays used to measure the ability of retinoids to control cell differentiation, namely, the reversal of keratinization in tracheal organ culture from vitamin A deficient hamsters and the inhibition of the induction of mouse epidermal ornithine decarboxylase by a tumor promoter.These compounds had bonds corresponding to selected bonds of the E-tetraene chain of retinoic acid (1) held in a planar cisoid conformation by inclusion in an aromatic ring.The meta-substituted analogue 3 of 4-benzoic acid (2) was far less active than 2 in both assays.In contrast, the vinyl homologue of 2 (4) and the 7,8-dihydro and 7,8-methano analogues (5 and 6) had activity comparable to that of 2.Analogues of 4-benzoic acid (7) were also screened.Replacement of the tetrahydronaphthalene ring of 7 by a benzonorbornenyl group (9) significantly reduced activity, as did removal of the vinylic methyl group from 9 (10).Replacement of the propenyl group of 9 by a cyclopropane ring (12) also reduced activity.Replacement of the tetrahydronaphthalene ring of 7 by 4,4-dimethyl-3,4-dihydro-2H-1-benzopyran and -benzothiopyran rings (13 and 14) also decreased activity.Inclusion of the 7,9 double bond system of 1 in an aromatic ring (15 and 16) reduced activity, whereas inclusion of the 5,7 double bond system in an aromatic ring enhanced activity (7 and 19).Inclusion of the 11,13 and 9,11,13 double bond systems in aromatic rings (2 and 18) also reduced activity below that of 1.Retinoic acid, 7, 13, 14, and 19 inhibited papilloma tumor formation in mice.Toxicity testing indicated that 7 was more toxic than 1, 13, 14, and 19, 19 was more toxic than 1, and 13 and 14 were less toxic than 1.