4521-33-9

Usage

Uses

Used in Pharmaceutical Industry:
5-NITROTHIOPHENE-2-CARBOXALDEHYDE is used as a reagent for the synthesis of mefloquine-oxazolidine derivatives, which exhibit activity against multidrug-resistant Mycobacterium tuberculosis. Its presence in the synthesis process aids in the development of new treatments for drug-resistant tuberculosis.
Used in Organic Chemistry:
5-NITROTHIOPHENE-2-CARBOXALDEHYDE is used in the preparation of 2,3-dihydro-2-(5-nitro-2-thienyl)quinazolin-4(1H)-ones and various novel oxime ether derivatives. These compounds have potential applications as anti-protozoan agents, contributing to the development of treatments for parasitic infections.

InChI:InChI=1/C5H3NO3S/c7-3-4-1-2-5(10-4)6(8)9/h1-3H

Synthetic route

(5-nitrothiophen-2-yl)methanol (20898-85-5) → 5-nitro-2-thiophenecarboxaldehyde (4521-33-9)

Conditions	Yield
With silica-supported Jones reagent In dichloromethane for 0.00269444h;	99.8%

5-nitrothiophene-2-carboxaldehyde diacetate (14289-24-8) → 5-nitro-2-thiophenecarboxaldehyde (4521-33-9)

Conditions	Yield
With hydrogenchloride In methanol; water at 65℃; for 8h;	80%
With ethanol; sulfuric acid
With hydrogenchloride
With sulfuric acid

2-(chloromethyl)-5-nitrothiophene (20898-86-6) + 2-lithio-2-nitropropane (147225-22-7) → 5-nitro-2-thiophenecarboxaldehyde (4521-33-9) + 2-isopropylidenemethyl-5-nitrothiophene (74786-70-2) + 2-(2-methyl-2-nitropropyl)-5-nitrothiophene + 1,2-bis-(5-nitro-2-thienyl)ethylene

Conditions	Yield
In methanol for 0.25h; Ambient temperature; Irradiation;	A n/a B 61% C 7% D 5%

2-(chloromethyl)-5-nitrothiophene (20898-86-6) → 5-nitro-2-thiophenecarboxaldehyde (4521-33-9) + 2-isopropylidenemethyl-5-nitrothiophene (74786-70-2) + 2-(2-methyl-2-nitropropyl)-5-nitrothiophene + 1,2-bis-(5-nitro-2-thienyl)ethylene

Conditions	Yield
With lithium 2-nitropropane In methanol for 0.25h; Ambient temperature; Irradiation;	A n/a B 61% C 7% D 5%

thiophene-2-carbaldehyde (98-03-3) → 5-nitro-2-thiophenecarboxaldehyde (4521-33-9) + 4-nitrothiophene-2-carbaldehyde (57500-53-5)

Conditions	Yield
With sulfuric acid; nitric acid at 0℃; for 0.5h;	A 13% B 46%
With sulfuric acid; nitric acid at -10℃; for 0.0833333h;	A n/a B 40%
With sulfuric acid; potassium nitrate at 0℃; for 0.5h; Inert atmosphere; Schlenk technique;	A n/a B 40%

2-(1'-chloro-2',2'-dimethylpropyl)-5-nitrothiophene (87207-17-8) → 5-nitro-2-thiophenecarboxaldehyde (4521-33-9) + 2,2-dimethyl-1-(5'-nitro-2'-thienyl)-1-propanol (87207-23-6) + 2,2-dimethyl-1-(5'-nitro-2'-thienyl)-propane-1-one (83054-95-9)

Conditions	Yield
With 2-lithio-2-nitropropane In dimethyl sulfoxide at 20℃; for 1.1h;	A 7% B 7% C 42%
With 2-lithio-2-nitropropane In dimethyl sulfoxide at 20℃; for 1.1h; Mechanism; Irradiation;	A 7% B 5% C 42%

(5'-nitro-2'-thienyl)methyl acetate (20898-83-3) → 5-nitro-2-thiophenecarboxaldehyde (4521-33-9)

Conditions	Yield
With sodium thiophenolate In dimethyl sulfoxide for 0.2h;	15%

2-(chloromethyl)-5-nitrothiophene (20898-86-6) → 5-nitro-2-thiophenecarboxaldehyde (4521-33-9)

Conditions	Yield
With sodium thiophenolate In dimethyl sulfoxide for 0.166667h;	7%

thiophene-2-carbaldehyde (98-03-3) → 5-nitro-2-thiophenecarboxaldehyde (4521-33-9)

Conditions	Yield
With nitric acid; acetic anhydride at -14℃; Kinetics; Rate constant; Thermodynamic data; other temperatures, E, lg A, ΔH(excit.), ΔS(excit.);

thiophene-2-carbaldehyde (98-03-3) + sulfuric acid (7664-93-9) + nitric acid (7697-37-2) → 5-nitro-2-thiophenecarboxaldehyde (4521-33-9) + 4-nitrothiophene-2-carbaldehyde (57500-53-5)

thiophene-2-carbaldehyde (98-03-3) + nitric acid (7697-37-2) + acetic anhydride (108-24-7) + acetic acid (64-19-7) → 5-nitro-2-thiophenecarboxaldehyde (4521-33-9) + 4-nitrothiophene-2-carbaldehyde (57500-53-5)

Conditions	Yield
anschl. Hydrolyse;

thiophene-2-carbaldehyde (98-03-3) → 5-nitro-2-thiophenecarboxaldehyde (4521-33-9) + 4-nitrothiophene-2-carbaldehyde (57500-53-5) + 3-nitrothiophene-2-carbaldehyde (58963-75-0)

Conditions	Yield
With sulfuric acid; nitric acid at 0℃; Title compound not separated from byproducts;

2,2-dimethyl-1-(2-thienyl)-1-propanone (20409-48-7) → 5-nitro-2-thiophenecarboxaldehyde (4521-33-9)

Conditions	Yield
Multi-step reaction with 4 steps 3: 95 percent / SOCl2 / pyridine 4: 7 percent / 2-lithio-2-nitropropane / dimethylsulfoxide / 1.1 h / 20 °C / Irradiation View Scheme

2,2-dimethyl-1-(5'-nitro-2'-thienyl)-1-propanol (87207-23-6) → 5-nitro-2-thiophenecarboxaldehyde (4521-33-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 95 percent / SOCl2 / pyridine 2: 7 percent / 2-lithio-2-nitropropane / dimethylsulfoxide / 1.1 h / 20 °C / Irradiation View Scheme

2,2-dimethyl-1-(5'-nitro-2'-thienyl)-propane-1-one (83054-95-9) → 5-nitro-2-thiophenecarboxaldehyde (4521-33-9)

Conditions	Yield
Multi-step reaction with 3 steps 2: 95 percent / SOCl2 / pyridine 3: 7 percent / 2-lithio-2-nitropropane / dimethylsulfoxide / 1.1 h / 20 °C / Irradiation View Scheme

2-thiophenecarboxaldehyde diacetate (63011-97-2) → 5-nitro-2-thiophenecarboxaldehyde (4521-33-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid anhydride; nitric acid; acetic acid 2: aqueous sulfuric acid View Scheme

methanol (67-56-1) + 5-nitro-2-thiophenecarboxaldehyde (4521-33-9) → 5-(dimethoxymethyl)-2-nitrothiophene (17375-68-7)

Conditions	Yield
With hydrogenchloride for 0.75h; Heating;	100%

5-nitro-2-thiophenecarboxaldehyde (4521-33-9) + trimethyl orthoformate (149-73-5) → 5-(dimethoxymethyl)-2-nitrothiophene (17375-68-7)

Conditions	Yield
With amberlyst-15 In acetonitrile for 1h; electroosmos;	99.8%
With amberlyst-15 In acetonitrile for 0.166667h;	97.5%

5-nitro-2-thiophenecarboxaldehyde (4521-33-9) + 4-allyl-3-thiosemicarbazide (3766-55-0) → 4-allyl-1-(5-nitrothenylidene)thiosemicarbazide (1198748-12-7)

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 20℃;	99%

5-nitro-2-thiophenecarboxaldehyde (4521-33-9) → 5-nitrothiophene-2-carboxylic acid (6317-37-9)

Conditions	Yield
With bromine; sodium acetate; acetic acid	98.5%
With hydrogenchloride; bromine; sodium hydroxide In water	98.2%
With sodium hypobromide; sodium acetate; acetic acid	92%

5-nitro-2-thiophenecarboxaldehyde (4521-33-9) + thiosemicarbazide (79-19-6) → 2-((5-nitrothiophen-2-yl)methylene)hydrazinecarbothioamide (5351-83-7)

Conditions	Yield
In methanol for 3h; Reflux;	98%
In ethanol for 2h; Reflux;	92%
With acetic acid In methanol for 2h; Reflux;	84.2%

4-amino-1,2,4-triazole (584-13-4) + 5-nitro-2-thiophenecarboxaldehyde (4521-33-9) → (5-nitro-thiophen-2-ylmethylene)-[1,2,4]triazol-4-yl-amine (31539-41-0)

Conditions	Yield
With toluene-4-sulfonic acid In toluene Heating;	98%
In ethanol for 0.5h; heating on a steam bath;	69%

5-nitro-2-thiophenecarboxaldehyde (4521-33-9) + 3-trifluoromethylaniline (98-16-8) → N-(5-nitro-2-thienomethylidene)-3-trifluoromethylaniline (140436-71-1)

Conditions	Yield
In ethanol for 1h; Heating;	98%

5-nitro-2-thiophenecarboxaldehyde (4521-33-9) + furan-2-ylmethanamine (617-89-0) → Furan-2-ylmethyl-[1-(5-nitro-thiophen-2-yl)-meth-(E)-ylidene]-amine (69819-72-3)

Conditions	Yield
Duolite A 101 D resin In 1,2-dimethoxyethane at -20 - 25℃; for 3h;	98%

5-nitro-2-thiophenecarboxaldehyde (4521-33-9) + 1,3-diaminoguanidine hydrochloride (36062-19-8) → 1,3-bis-((5-nitrothiophen-2-yl-methylidene)amino)guanidine hydrochloride (1206770-32-2)

Conditions	Yield
In methanol for 5h; Reflux;	98%

5-nitro-2-thiophenecarboxaldehyde (4521-33-9) → 5-nitrothiophene-2-carbaldehyde oxime (6030-18-8)

Conditions	Yield
With hydroxylamine hydrochloride; potassium carbonate In water Reflux;	98%
With pyridine; hydroxylamine hydrochloride In ethanol for 24h; Reflux;	85%
With hydroxylamine hydrochloride; sodium carbonate In dimethyl sulfoxide at 20℃;
With hydroxylamine hydrochloride In methanol at 25℃; for 0.25h;

2,4-imidazolidinedione (461-72-3) + 5-nitro-2-thiophenecarboxaldehyde (4521-33-9) → (Z)-5-((5-nitrothiophen-2-yl)methylene)imidazolidine-2,4-dione

Conditions	Yield
With copper(II)-Para-aminobenzoic acid complex supported on Fe3O4 Magnetic nanoparticle In ethanol for 1.55h; Aldol Condensation; Reflux; Green chemistry;	98%

5-nitro-2-thiophenecarboxaldehyde (4521-33-9) → (5-nitrothiophen-2-yl)methanol (20898-85-5)

Conditions	Yield
With sodium tetrahydroborate In ethanol for 5h;	97.2%
Stage #1: 5-nitro-2-thiophenecarboxaldehyde With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 0 - 20℃; for 20h; Inert atmosphere; Stage #2: With sodium tetrahydroborate In 1,2-dichloro-ethane at 20℃; for 0.5h; Inert atmosphere;	96%
With sodium tetrahydroborate In methanol at 0 - 20℃; Inert atmosphere;	90%

Hippuric Acid (495-69-2) + 5-nitro-2-thiophenecarboxaldehyde (4521-33-9) → 4-[1-(5-Nitro-thiophen-2-yl)-meth-(Z)-ylidene]-2-phenyl-4H-oxazol-5-one (31271-16-6, 89035-35-8)

Conditions	Yield
With sodium acetate; acetic anhydride at 100℃; for 2h;	97%

5-nitro-2-thiophenecarboxaldehyde (4521-33-9) + 4-chloro-aniline (106-47-8) → N-(5-nitro-2-thienomethylidene)-4-chloroaniline (64857-14-3)

Conditions	Yield
In ethanol for 1h; Heating;	97%

5-nitro-2-thiophenecarboxaldehyde (4521-33-9) + 3-amino-2-(4-chloro-2-ethylthio-5-methylbenzenesulphonyl)guanidine (519053-87-3) → 1-(4-chloro-2-ethylthio-5-methylbenzenesulfonyl)-3-(5-nitrothienylideneamino)guanidine

Conditions	Yield
In ethanol for 4h; Heating;	97%

5-nitro-2-thiophenecarboxaldehyde (4521-33-9) + 1,2-dichloro-ethane (107-06-2) → methyl 5-nitrothiophene-2-carboxylate (5832-01-9)

Conditions	Yield
With iodine; sodium hydrogencarbonate In methanol; n-heptane	96.5%

2,4-thiazolidinedion (2295-31-0) + 5-nitro-2-thiophenecarboxaldehyde (4521-33-9) → (Z)-5-((5-nitrothiophen-2-yl)methylene)thiazolidine-2,4-dione

Conditions	Yield
With copper(II)-Para-aminobenzoic acid complex supported on Fe3O4 Magnetic nanoparticle In ethanol for 1.56667h; Aldol Condensation; Reflux; Green chemistry;	96%

2-amino-5-ethyl-1,3,4-thiadiazole (14068-53-2) + 5-nitro-2-thiophenecarboxaldehyde (4521-33-9) + phosphonic acid diethyl ester (762-04-9) → diethyl (((5-ethyl-1,3,4-thiadiazol-2-yl)amino)(5-nitrothiophen-2-yl)methyl)phosphonate

Conditions	Yield
With phospho sulphonic acid In neat (no solvent) for 0.15h; Kabachnik-Fields Reaction; Microwave irradiation; Green chemistry;	95.5%

5-nitro-2-thiophenecarboxaldehyde (4521-33-9) + 4-hydroxybenzoic acid hydrazide (5351-23-5) → 4-hydroxybenzoic acid (5-nitrothiophen-2-ylmethylene)hydrazide

Conditions	Yield
acetic acid In ethanol for 4h; Heating / reflux;	95%
In ethanol; water Heating;	86%

5-nitro-2-thiophenecarboxaldehyde (4521-33-9) + 4-Phenyl-3-thiosemicarbazide (5351-69-9) → (E)-4-phenyl-1-(5-nitrothienyl)thiosemicarbazide

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 20℃; Inert atmosphere;	95%

5-nitro-2-thiophenecarboxaldehyde (4521-33-9) + [{5-(4-benzylthio-2-chloro-5-sulfamoylphenyl)-1,3,4-oxadiazol-2-yl}methyl]triphenylphosphonium chloride → (E)-2-(benzylthio)-4-chloro-5-(5-(2-(5-nitrothiophen-2-yl)vinyl)-1,3,4-oxadiazol-2-yl)benzenesulfonamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 24h; Wittig Olefination; Inert atmosphere;	95%

5-nitro-2-thiophenecarboxaldehyde (4521-33-9) + adamantane-1-carbohydrazide (17846-15-0) → E-N'-[(5-nitrothiophen-2-yl)methylidene]adamantane-1-carbohydrazide

Conditions	Yield
In ethanol for 1h; Reflux;	95%

5-nitro-2-thiophenecarboxaldehyde (4521-33-9) + phenethylamine (64-04-0) → [1-(5-Nitro-thiophen-2-yl)-meth-(E)-ylidene]-phenethyl-amine (69819-75-6)

Conditions	Yield
Duolite A 101 D resin In 1,2-dimethoxyethane at -20 - 25℃; for 3h;	94%

(cyclohexa-2,4-dienyl-diphenyl-λ5-phosphanylidene)-acetic acid tert-butyl ester + 5-nitro-2-thiophenecarboxaldehyde (4521-33-9) → 3-(5-nitro-thiophen-2-yl)-acrylic acid tert-butyl ester

Conditions	Yield
In water at 20℃; for 1h; Wittig reaction;	94%

5-nitro-2-thiophenecarboxaldehyde (4521-33-9) + 2,5-diamino-thiophene-3,4-dicarboxylic acid diethyl ester (80691-81-2) → 2-amino-5-[(5-nitrothiophen-2-ylmethylene)amino]thiophene-3,4-dicarboxylic acid diethyl ester

Conditions	Yield
In toluene for 0.5h; Reflux;	94%
With trifluoroacetic acid In isopropyl alcohol for 0.5h; Heating;	87%

5-nitro-2-thiophenecarboxaldehyde (4521-33-9) + dimedone (126-81-8) + 1,2-diamino-benzene (95-54-5) → 3,3-dimethyl-11-(5-nitrothiophen-2-yl)-2,3,4,5,10,11-hexahydro-1Hdibenzo[b,e][1,4]diazepin-1-one

Conditions	Yield
With silica-supported nickel oxide nanocomposites In ethanol at 70℃; for 0.25h; Microwave irradiation; Green chemistry;	94%

5-nitro-2-thiophenecarboxaldehyde (4521-33-9) + p-toluic hydrazide (3619-22-5) → (E)-4-methyl-N′-((5-nitrothiophen-2-yl)methylene)benzohydrazide

Conditions	Yield
In ethanol; water Heating;	93%
With acetic acid In methanol for 6h; Reflux;	80%

5-nitro-2-thiophenecarboxaldehyde (4521-33-9) + 4-aminobenzohydrazide (5351-17-7) → C12H10N4O3S

Conditions	Yield
In ethanol; water Heating;	93%

5-nitro-2-thiophenecarboxaldehyde (4521-33-9) + 3-chlorobenzhydrazide (1673-47-8) → C12H8ClN3O3S

Conditions	Yield
In ethanol; water Heating;	93%

Upstream product

• 98-03-3 thiophene-2-carbaldehyde 
• 14289-24-8 5-nitrothiophene-2-carboxaldehyde diacetate 
• 20898-83-3 (5'-nitro-2'-thienyl)methyl acetate 
• 20898-86-6 2-(chloromethyl)-5-nitrothiophene 
• 147225-22-7 2-lithio-2-nitropropane 
• 87207-17-8 2-(1'-chloro-2',2'-dimethylpropyl)-5-nitrothiophene 
• 7664-93-9 sulfuric acid 
• 7697-37-2 nitric acid 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 20898-85-5 (5-nitrothiophen-2-yl)methanol 
• 20409-48-7 2,2-dimethyl-1-(2-thienyl)-1-propanone 
• 83054-95-9 2,2-dimethyl-1-(5'-nitro-2'-thienyl)-propane-1-one 
• 63011-97-2 2-thiophenecarboxaldehyde diacetate 

Downstream Products

• 50868-70-7 (E)-3-(2-nitrothiophen-5-yl)propenoic acid 
• 42826-38-0 1-(5-nitro-[2]thienylmethylenamino)-piperidine 
• 6286-12-0 5-nitro-2-thiophene semicarbazone 
• 5351-83-7 2-((5-nitrothiophen-2-yl)methylene)hydrazinecarbothioamide 
• 91093-51-5 5-nitro-thiophene-2-carbaldehyde phenylhydrazone 
• 81747-04-8 5-nitro-thiophene-2-carbaldehyde-(2,4-dinitro-phenylhydrazone) 
• 91182-63-7 5-nitro-thiophene-2-carbaldehyde-(4-bromo-phenylhydrazone) 
• 84653-70-3 2-(5-nitrothiophen-2-ylmethylene)malononitrile 
• 6317-37-9 5-nitrothiophene-2-carboxylic acid 
• 4601-06-3 2-[2-(5-nitro-thiophen-2-yl)-vinyl]-pyridine 
• 50832-68-3 1-acetyl-2-[2-(5-nitro-thiophen-2-yl)-vinyl]-1H-imidazole 
• 31271-16-6 4-[1-(5-Nitro-thiophen-2-yl)-meth-(Z)-ylidene]-2-phenyl-4H-oxazol-5-one 
• 107505-22-6 C₂₅H₂₉N₅O₂S 
• 140436-72-2 N-(5-nitro-2-thienomethylidene)-4-trifluoromethylaniline 

Relevant academic research and scientific papers

Cyrhetrenylaniline and new organometallic phenylimines derived from 4- and 5-nitrothiophene: Synthesis, characterization, X-Ray structures, electrochemistry and in vitro anti-T. brucei activity

A novel series of cyrhetrenyl (3a-4a) and ferrocenyl (3b-4b) Schiff bases were synthesized through a condensation reaction, between the known 4-ferrocenylaniline (2b) or the unreported 4-cyhretrenylaniline (2a) with 4- or 5-nitrothiophenecarboxaldehyde. The structure of 2a and the new Schiff bases have been elucidated using conventional spectroscopic techniques (FT-IR, 1H and 13C NMR), mass spectrometry, and single-crystal X-ray diffraction analysis of compounds 2a, 4a and 3b. Cyclic voltammetry of organometallic phenylimines derived from 5-nitrothiophene showed NO2 group reduction potentials (E1/2 ≈ ?0.575 V) that were more anodic than those registered for their 4-nitro analogues (E1/2 ≈ ?0.981 V). All organometallic imines were tested against the bloodstream form of Trypanosoma brucei. Evaluation indicated that the most active complexes are the 5-nitrothiophene derivatives, 4a, which were remarkably more active than nifurtimox. In addition, complex 4b resulted in less toxicity to host L6 cells than nifurtimox. The results revealed that the electronic effects of cyrhetrene and ferrocene are not an influential factor in E1/2 and anti-Trypanosoma brucei activity for these new imines, which is probably due to the non-coplanarity of the [(η5-C5H4)-C6H4-N=CH-(C4H2S)] system.

Synthesis method of 5-nitrothiophene-2-formaldehyde

The invention relates to the technical field of chemistry, in particular to a synthesis method of 5-nitrothiophene-2-formaldehyde. The method comprises the steps of mixing 2-thiophenecarboxaldehyde and acetic anhydride, carrying out nucleophilic addition reaction to generate (acetyloxy) (2-thiophene) methyl acetate, and adding a nitrating agent to carry out nitration reaction to prepare 5-nitrothiophene-2-yl methylene diacetate; and carrying out a hydrolysis reaction on the obtained 5-nitrothiophene-2-yl methylene diacetate in a solvent to prepare 5-nitrothiophene-2-formaldehyde. The method has the beneficial effects that (1) cheap and easily available raw materials are used, the process is simple, the production cost is low, and the method is suitable for industrial production; and (2) the total yield and the total purity of the product are high.

Synthesis, protolytic equilibria, and antimicrobial action of nifuroxazide analogs

The present paper reports on the synthesis of four hydrazones derived from 5-nitro-2-furfural, 5-nitro-2-thiophenal, isoniazid, 2,4- and 3,4-dihydroxy-N′-methylenebenzohydrazide. The acid-base dissociation constants of these compounds were determined in an aqueous solution. The protolytic equilibria-related ability of hydrazones to “sense” anions in dimethyl sulfoxide-containing water of different concentrations is studied using spectrophotometry, NMR spectroscopy, and quantum chemistry methods. The antimicrobial action of the hydrazones was tested and compared with that of the known drug nifuroxazide.

Ethylammonium nitrate (EAN)/Tf2O and EAN/TFAA: Ionic liquid based systems for aromatic nitration

Acting as in situ sources of triflyl nitrate (TfONO2) and trifluoroacetyl nitrate (CF3COONO2), the EAN/Tf 2O and EAN/TFAA systems, generated via metathesis in the readily available ethylammonium nitrate (EAN) ionic liquid as solvent, are powerful electrophilic nitrating reagents for a wide variety of aromatic and heteroaromatic compounds. Comparative nitration experiments indicate that EAN/Tf2O is superior to EAN/TFAA for nitration of strongly deactivated systems. Both systems exhibit low substrate selectivity (K T/KB = 5-10) in (Figure presented) between values reported for covalent nitrates and preformed nitronium salts.

SMALL MOLECULE INHIBITORS OF PROTEIN ARGININE METHYLTRANSFERASES (PRMTS)

The present invention relates to compounds that are useful as inhibitors of protein arginine methyltransferase that have a formula selected from Formula (I), Formula (II) and Formula (III), as well as racemic mixtures, diastereomers, enantiomers and tautomers thereof and N-oxides, hydrates, solvates, pharmaceutically acceptable salts, prodrugs and complexes thereof as defined herein. Said compound are useful as inhibitors of PRMTs and/or CARM-I. The invention further relates to compositions comprising such compounds and methods for their use.

Synthesis of the fused heterobicycles 5-pyridin-2-yl-thieno[3,2-b]pyridine, 6-pyridin-2-yl-thieno[2,3-b]pyridine and 6-pyridin-2-yl-thieno[3,2-c]pyridine

Three new pyridyl thienopyridines, 5-pyridin-2-yl-thieno[3,2-b]pyridine, 6-pyridin-2-yl-thieno[2,3-b]pyridine and 6-pyridin-2-yl-thieno[3,2-c]pyridine, have been synthesized, each through a different synthetic sequence. Overall yields ranged from 8% to 32%. Georg Thieme Verlag Stuttgart.

Clean and selective oxidation of aromatic alcohols using silica-supported Jones' reagent in a pressure-driven flow reactor

By exploiting the high surface to volume ratio obtained within continuous flow reactors, we are able to oxidise selectively an array of primary alcohols to either the aldehyde or carboxylic acid, depending on the flow rates employed, demonstrating a degree of reaction control unattainable in traditional stirred reactors.

COMBRETASTATIN DERIVATIVES WITH CYTOTOXIC ACTION

The invention described herein relates to new combretastatin derivatives obtained by total synthesis and having the following general formula (I) in which the groups are as defined in the description here below. Said compounds, though chemically related to the structure of cis/trans-combretastatin, do not always bind tubulin, but nevertheless exhibit cytotoxic activity of interest in the oncological field as anticancer and/or antiangiogenic agents.

Cerebral antihypoxic activity of new thienyldihydropyridines

New thienyldihydropyridines were synthesized according to Hantzsch's method. The antihypoxic activity of these compounds was compared with that of three reference phenyldihydropyridines by means of the skin conductance reaction (SCR)-hypoxia test.