3034-52-4

Usage

Chemical Properties

Pale yellow liquid

InChI:InChI=1/C3H2ClNS/c4-3-5-1-2-6-3/h1-2H

Upstream product

• 288-47-1 1,3-thiazole 
• 96-50-4 2-thiazolylamine 
• 7647-01-0 hydrogenchloride 
• 141305-44-4 thiazole 3-oxide 

Downstream Products

• 104396-29-4 (3-methoxy-phenyl)-thiazol-2-yl-acetonitrile 
• 874509-08-7 [4-(4-nitro-benzenesulfonyl)-phenyl]-thiazol-2-yl-amine 
• 100974-07-0 4-dimethylamino-2-phenyl-2-thiazol-2-yl-butyronitrile 
• 99974-30-8 2-phenyl-2-(thiazol-2-yl)acetonitrile 
• 54670-80-3 N-(thiazol-2-yl)pyridin-2-amine 
• 288-47-1 1,3-thiazole 
• 14542-13-3 2-methoxythiazole 
• 88917-11-7 2-chloro-1,3-thiazole-5-sulfonyl chloride 
• 329794-40-3 2-chloro-5-phenyl-thiazole 
• 1005-28-3 2-(dimethylamino)thiazole-5-carbaldehyde 
• 95453-58-0 2-chloro-1,3-thiazole-5-carbaldehyde 
• 56355-16-9 ethyl 2-[4-(2-thiazolyloxy)-phenyl]propionate 
• 72605-86-8 2-chlorothiazole-5-carboxylic acid methyl ester 
• 1189999-01-6 C₁₁H₉NO₃S 

Relevant academic research and scientific papers

TYROSINE KINASE INHIBITORS CONTAINING A ZINC BINDING MOIETY

The present invention relates to tyrosine kinase inhibitors that contain a zinc-binding moiety and their use in the treatment of tyrosine related diseases and disorders such as cancer. The said derivatives may further act as HDAC inhibitors.

INHIBITORS OF PROTEIN KINASES

The invention provides inhibitors of protein kinases, such as an Src kinase, enzymes which has been implicated in processes such as cell migration, proliferation, and survival. The inhibitors include 2,5-disubstituted derivatives of thiazole wherein the substituents are as defined. The invention also provides a method of using the inhibitors in treatment of cancer, and a method of preparation of the inhibitors by a palladium-catalyzed coupling reaction.

Cyclic protein tyrosine kinase inhibitors

Novel cyclic compounds and salts thereof, pharmaceutical compositions containing such compounds, and methods of using such compounds in the treatment of protein tyrosine kinase-associated disorders such as immunologic and oncologic disorders.

Dehydroamino acids

Compounds of formula 1 and 1-1, wherein R1 is hydrogen, hydroxy, amino or halogen, R2 is hydrogen, hydroxy, or halogen and R3 is hydrogen (Formula 1) or R1 is hydrogen and R2 and R3 taken together with the ethenylene group connecting them form phenyl, pyrrole, pyrroline, oxopyrroline, pyrazole, triazole, or imidazole (Formula 1-1), A is R4 R5 are hydrogen, methyl, ethyl or halogen except that R4 r5 cannot both be hydrogen; and 1) B is hydrogen, or lower alkyl; or 2) B is where R6 R7 R8 and R9 are independently hydrogen, hydroxy, aminosulfonyl, halogen, lower alkoxy, cyano, amino, lower alkyl, lower alkyl amino, or nitro; or 3) B is where R10 is hydrogen, hydroxy, halogen, or lower alkyl and C is a five- or six- membered ring with 0 to 3 heteroatoms which heteroatoms are selected from nitrogen, oxygen, and sulfur, which ring may be unsubstituted or mono- or di- substituted with lower alkyl, cycloalkyl, amino, or substituted amino; 4) B is where X and Y are independently methylene or nitrogen; or 5) B is where at leat one of T, U, V, or W is nitrogen, and any of T, U, V or W which is carbon may be substituted with lower alkyl, lower alkyl amino, lower alkoxy, hydroxy, aminosulfonyl, halogen, cyano, amino, or nitro; or 6) B is where Y is carbon or nitrogen; or 7) B is a five-membered aromatic ring with 1 to 3 heteratoms selected from nitrogen, oxygen, and sulfur which ring may be unsubstituted or mono- or di-substituted with lower alkyl, cycloalky, trifluoroloweralkyl, amino, halogen, substituted amino, or which ring may be fused with a 5 or 6 membered aromatic ring containing 0 to 3 heteroatoms which heteroatoms are selected from nitrogen, oxygen, and sulfur; and pharmaceutically acceptable salts thereof, and related prodrugs, pharmaceutical compositions and methods of treatment, which compounds are useful for treating psoriasis.

Tetrahalogenomethanes: Simple reagents for the synthesis of monohalogenated and mixed dihalogenated aromatic heterocycles via metal-halogen exchange from lithium compounds

Tetrabromo- or tetrachloromethane and 2-lithio derivatives of aromatic heterocycles rapidly produce the corresponding 2-bromo or 2-chloro derivatives in high yields through a metal-halogen exchange mechanism. This kind of reaction was also used to obtain, in good yields, 5-bromo-2-chlorothiazole and 5-bromo-2-chloro-N-methylimidazole.

A new synthesis of chloroheterocycles via metal-halogen exchange between trichloroacetyl derivatives and heteroaromatic lithium and Grignard reagents

The reaction between 2-lithio derivatives of aromatic azaheterocycles and trichlorocetyl derivatives rapidly produces the corresponding 2-chloro derivatives in high yields through a metal-halogen exchange mechanism. The use of ethyl trichloroacetate can give better results with respect to those obtained with trichloroacetyl chloride, which probably involves dichloroketene formation. The reaction with Grignard reagents is more complex: in fact, 2-benzothiazolylmagnesium chloride with ethyl trichloroacetate or trichloroacetyl chloride gives 2-chlorobenzothiazole together with considerable amounts of ethyl 1,3-benzothiazole-2-carboxylate or 2-benzothiazolyl dichloromethyl ketone, respectively.

Fungicides for the control of take-all disease of plants

A method of controlling Take-All disease of plants by applying a fungicide of the formula STR1 wherein Z1 and Z2 are C and are part of an aromatic ring which is benzothiophene; and A is selected from --C(X)-amine wherein the amine is an unsubstituted, monosubstituted or disubstituted amino radical, --C(O)--SR3, --NH--C(X)R4, and --C(=NR3)--XR7 ; B is --Wm --Q(R2)3 or selected from O-tolyl, 1-naphthyl, 2-naphthyl, and 9-phenanthryl, each optionally substituted with halogen or R4 ; Q is C, Si, Ge, or Sn; W is --C(R3)p H(2-p) --; or when Q is C, W is selected from --C(R3)p H(2-p), --N(R3)m H(1-m)--, --S(O)p--, and --O--; X is 0 or S; n is 0, 1, 2, or 3; m is 0 or 1; p is 0, 1, or 2; each R and R2 is independently defined herein; R3 is C1 -C4 alkyl; R4 is C1 -C4 alkyl, haloalkyl, alkoxy, alkylthio, alkylamino, or dialkylamino; and R7 is C1 -C4 alkyl, haloalkyl, or phenyl, optionally substituted with halo, nitro, or R4 ; or an agronomic salt thereof.

New Methods for the Introduction of Substituents into Thiazoles

New methods for the regioselective introduction of substituents into thiazoles have been developed using thiazole, 2-phenylthiazole and 4,5-dimethylthiazole as representative thiazoles.Improved halogenation methods, displacement of hydroxy groups in combination with dehalogenation at C-5 yield all eight possible 2-phenyl-4-halo-, 5-halo and 4,5-dihalo-thiazoles in which halogen is chlorine and bromine.Peracid oxidation of the thiazoles gives the corresponding thiazole 3-oxides.These are not activated towards halogenation but are deprotonated with sodium hydride.The anion formed react with electrophiles such as paraformaldehyde, 2,2-dimethylpropanal, 2,2-dimethylpropanoyl chloride, hexachloroethane, tetrabromomethane, and dimethyl disulfide leading to the introduction of carbon substituents, halogen, and methylthio groups.In these reactions, the reactivity of the thiazole ring positions decreases in the order 2 than 5 than 4.Monoselectivity is low when halogen and methylthio groups are introduced since these substituents enhance the acidity of adjacent ring protons. 2-Phenyl-4,5-dihalothiazole 3-oxides lose the 5-halogen when treated with sulfite ion.Trimethyloxonium tetrafluoroborate O-methylates thiazole 3-oxides.Thiazole N-oxides also react with acetyl chloride and phosphorus oxychloride to afford chlorothiazoles in a non-selective manner.Phosphorus trichloride deoxygenates thiazole 3-oxides.