82127-11-5

Upstream product

• 39145-35-2 2-cyano-3-thiophen-2-yl-thioacrylamide 
• 5447-87-0 2-(1-phenylethylidene)propanedinitrile 
• 82127-07-9 2-bromo-6-(2-thienyl)-4-phenyl-3-cyanopyridine 
• 88-15-3 2-Acetylthiophene 
• 40219-06-5 benzylidenecyanothioacetamide 
• 7357-70-2 Cyanothioacetamide 
• 3988-77-0 2-cinnamoylthiophene 
• 109830-72-0 C₁₆H₁₀N₂S 
• 2910-81-8 3-(2'-thienyl)acrylophenone 
• 100-52-7 benzaldehyde 
• 326-91-0 1,1,1-trifluoro-4-(2-thienyl)butane-2,4-dione 
• 68029-52-7 (E)-2-cyano-3-phenylprop-2-enethioamide 
• 3988-77-0 3-phenyl-1-thiophen-2-yl-propenone 
• 81829-55-2 2-(3-(2-thienyl)-3-oxo-1-phenylpropyl)malononitrile 

Downstream Products

• 82137-61-9 (3-cyano-4-phenyl-6-(2'-thienyl)-2-pyridinylthio)acetonitrile 
• 82127-22-8 3-amino-4-phenyl-6-(2'-thienyl)-thieno[2,3-b]pyridine-2-carbonitrile 
• 682334-33-4 [2-(3-cyano-4-phenyl-6-thiophen-2-yl-pyridin-2-ylsulfanyl)-acetylamino]-acetic acid 
• 682334-38-9 [(3-amino-4-phenyl-6-thiophen-2-yl-thieno[2,3-b]pyridine-2-carbonyl)-amino]-acetic acid 
• 847976-22-1 ethyl 2-((3-cyano-4-phenyl-6-(thiophen-2-yl)pyridin-2-yl)thio)acetate 
• 457958-42-8 3-cyano-2-methylthio-4-phenyl-6-(2-thienyl)pyridine 
• 539830-09-6 4-chloro-9-phenyl-7-(2'-thienyl)-pyrido[3',2':4,5]thieno[3,2-d][1,2,3]triazine 
• 539830-25-6 9-Phenyl-7-thiophen-2-yl-3H-pyrido[3',2':4,5]thieno[3,2-d][1,2,3]triazin-4-one 
• 539830-11-0 4-hydrazino-9-phenyl-7-(2'-thienyl)-pyrido[3',2':4,5]thieno[3,2-d][1,2,3]triazine 
• 539829-94-2 3-amino-4-phenyl-6-(2'-thienyl)-2-(1H-tetrazol-2'-yl)-thieno[2,3-b]pyridine 
• 539830-15-4 4-oxo-9-phenyl-1,2,3,4-tetrahydro-7-(2'-thienyl)-2-thioxopyrido[3',2':4,5]thieno[3,2-d]pyrimidine 
• 539829-92-0 3-amino-2-(4,5-dihydroimidazol-2-yl)-4-phenyl-6-(2'-thienyl)-thieno[2,3-b]pyridine 
• 539829-83-9 2,4-dithioxo-9-phenyl-1,2,3,4-tetrahydro-7-(2'-thienyl)-pyrido[3',2':4,5]thieno[3,2-d]pyrimidine 

Relevant academic research and scientific papers

Synthesis of substituted pyrido[3′,2′:4,5]thieno[3,2-c]isoquinolin-5(6H)-ones and their sulfinyl and sulfonyl derivatives

A method for the synthesis of previously unknown pyrido[3′,2′:4,5]thieno[3,2-c]isoquinolin-5(6H)-ones was suggested, which includes a condensation reaction of substituted 3-cyanopyridine-2(1H)-thiones with methyl 2-(chloromethyl)benzoate and subsequent treatment of the condensation products with potassium tert-butoxide. The oxidation of the condensation products to sulfoxides or sulfones and subsequent treatment of these compounds with potassium tert-butoxide led to substituted pyrido[3′,2′:4,5]thieno[3,2-c]isoquinolin-5(6H)-one 11-oxides or substituted pyrido[3′,2′:4,5]thieno[3,2-c]isoquinolin-5(6H)-one 11,11-dioxides.

COMPOSITIONS AND METHODS OF MODULATING SHORT-CHAIN DEHYDROGENASE ACTIVITY

Compounds and methods of modulating 15-PGDH activity, modulating tissue prostaglandin levels, treating disease, diseases disorders, or conditions in which it is desired to modulate 15-PGDH activity and/or prostaglandin levels include 15-PGDH inhibitors described herein.

INHIBITORS OF SHORT-CHAIN DEHYDROGENASE ACTIVITY FOR PROMOTING NEUROGENESIS AND INHIBITING NERVE CELL DEATH

A method of promoting neuroprotection in a subject from axonal degeneration, neuronal cell death, and/or glia cell damage after injury, augmenting neuronal signaling underlying learning and memory, stimulating neuronal regeneration after injury, and/or treating a disease, disorder, and/or condition of the nervous system in a subject in need thereof includes administering to the subject a therapeutically effective amount of a 15-PGDH inhibitor.

Inhibitors of 15-Prostaglandin Dehydrogenase To Potentiate Tissue Repair

The enzyme 15-prostaglandin dehydrogenase (15-PGDH) catalyzes the first step in the degradation of prostaglandins including PGE2. It is a negative regulator of tissue repair and regeneration in multiple organs. Accordingly, inhibitors of 15-PGDH are anticipated to elevate in vivo levels of PGE2 and to promote healing and tissue regeneration. The small molecule SW033291 (1) inhibits 15-PGDH with Ki = 0.1 nM in vitro, doubles PGE2 levels in vivo, and shows efficacy in mouse models of recovery from bone marrow transplantation, ulcerative colitis, and partial hepatectomy. Here we describe optimized variants of 1 with improved solubility, druglike properties, and in vivo activity.

INHIBITORS OF SHORT-CHAIN DEHYDROGENASE ACTIVITY FOR TREATING FIBROSIS

A method of treating or preventing a fibrotic disease, disorder or condition includes administering to a subject in need of treatment a 15-PGDH inhibitor.

COMPOSITIONS AND METHODS OF MODULATING SHORT-CHAIN DEHYDROGENASE ACTIVITY

Compounds and methods of modulating 15-PGDH activity, modulating tissue prostaglandin levels, treating disease, diseases disorders, or conditions in which it is desired to modulate 15-PGDH activity and/or prostaglandin levels include 15-PGDH inhibitors described herein.

COMPOSITIONS AND METHODS OF MODULATING 15-PGDH ACTIVITY

Compounds and methods of modulating 15-PGDH activity, modulating tissue prostaglandin levels, treating disease, diseases disorders, or conditions in which it is desired to modulate 15-PGDH activity and/or prostaglandin levels include 15-PGDH inhibitors and 15-PGDH activators described herein.

Studies on the synthesis of some new cyanopyridine-thione and thieno[2,3-b]pyridine derivatives

The work included in this article involves the synthesis of new cyanopyridinethiones as good synthons for new thieno[2,3-b]pyridines with anticipated biological activities. Thus, the reaction of -aryl - thiocarbamoylacrylonitrile (1a-c) with (2-thenoyl)-,-trifluoroacetone led to an unexpected formation of 4-aryl-3-cyano-6-(2-thienyl)pyridine-2(1H)-thiones (4a-c). In contrast, the reaction of 1a,b with ethyl acetoacetate produced 4-aryl-3-cyano-5-ethoxycarbonyl-6-methylpyridine-2(1H)-thiones (12a,b). The reaction of compound 4a with methyl iodide gave 2-methylthio derivative 6, which upon treatment with hydrazine hydrate furnished pyrazolopyridine 7. Treatment of 4a-c with chloroacetaimde, in the presence of sodium ethoxide, led to the formation of 3-amino-4-aryl-6-(2-thienyl)thieno[2,3-b]pyridine-2-carboxamides (8a-c). The reactions of 8a with some aromatic aldehydes and/or cycloalkanones were carried out and their products were identified. Compounds 12a,b were reacted with chloro-N-arylacetamides to give ethyl 4-aryl-2-(N-aryl) carbamoylmethylthio-3-cyano-6-methylpyridine-5-carboxylates (13a-j). Upon treatment of compounds 13a-j with sodium alkoxide in alcohol, they underwent an intramolecular Thorpe-Ziegler cyclization to furnish ethyl 3-amino-4-aryl-2-(N- aryl)carbamoyl-6-methylthieno[2,3-b]pyridine-5-carboxylates (14a-j). Compounds 14a-j, in turn, were reacted with triethyl orthoformate and/or carbon disulfide to give corresponding pyridothienopyrimidinone derivatives 15a-j and 18. Pyridothienotriazinone analogs 17a-j were synthesized via diazotisation of compounds 14a-j.

Synthesis and reactions of some new heterocyclic compounds containing the thienylthieno[2,3-b]pyridine moiety

(4-Aryl-3-cyano-6-(2-thienyl)pyridin-2-ylthio)acethydrazides (5a-c), 3-amino-4-aryl-6-(2-thienyl)thieno[2,3-b]pyridine-2-carbohydrazides (6a-c) and 3-amino-4-phenyl-6-(2-thienyl)thieno[2,3-b]pyridine-2-carboxylic acid (30) were prepared and employed as key intermediates in the synthesis of the title compounds.

Synthesis of some new pyridothienopyrimidines and related [1,2,4]triazolopyridothienopyrimidines

3-Amino-4-phenyl-6-(2-thienyl)thieno[2,3-b]pyridine-2-carboxamide (3a) reacted with triethyl orthoformate to give the pyrimidinone derivative 4. Reaction of 4 with phosphorus oxychloride produced the corresponding 4-chloropyrimidine derivative 5 which underwent some nucleophilic displacements upon treatment with thiourea, morpholine or aniline to give the pyridothienopyrimidine derivatives 6, 8 and 9 respectively. Similarly, the reaction of 5 with hydrazine hydrate afforded 4-hydrazino-9-phenyl-7-(2-thienyl)pyrido[3',2':4,5]thieno[3,2-d]pyrimidine (10). The condensation of 3-amino-4-phenyl-6-(2-thienyl)thieno[2,3-b]pyridine-2-carbonitrile (3b) with triethyl orthoformate led to the methanimidate derivative 18 which upon treatment with hydrazine hydrate furnished 3-amino-3,4-dihydro-4-imino-9-phenyl-7-(2-thienyl)pyrido[3',2':4,5]thieno[3,2-d]pyrimidine (19). The compounds 10 and 19 were used as precursors for synthesizing the isomeric [1,2,4]triazolopyridothienopyrimidines via Dimroth rearrangements.