14543-45-4

Usage

Uses

Used in Research Fields:
4-Amino-3-Mercaptobenzoic Acid is used as a research compound for studying cell defense mechanisms against oxidative stress. Its antioxidant property allows it to eliminate harmful free radicals, providing protection against oxidative stress.
Used in Laboratory Applications:
4-Amino-3-Mercaptobenzoic Acid is used as a metal-chelating agent for binding and removing heavy metals in laboratories. Its sulfur atom enables it to form bonds with metals, making it a useful agent in this context.
Used in Antioxidant Applications:
4-Amino-3-Mercaptobenzoic Acid is used as an antioxidant in various applications, where its ability to eliminate free radicals can help protect against oxidative stress and related damage.

InChI:InChI=1/C7H7NO2S/c8-5-2-1-4(7(9)10)3-6(5)11/h1-3,11H,8H2,(H,9,10)

Synthetic route

4-amino-3-thiocyanatobenzoic acid (18330-64-8) → 4-amino-3-mercaptobenzoic acid (14543-45-4)

Conditions	Yield
With sodium sulfide In ethanol; water at 90℃; for 2h;	96%
Multi-step reaction with 2 steps 1: hydrochloric acid / H2O / 0.5 h / Heating 2: potassium hydroxide / H2O / 4 h / Heating View Scheme

2-aminobenzo[d]thiazole-6-carboxylic acid methyl ester (66947-92-0) → 4-amino-3-mercaptobenzoic acid (14543-45-4)

Conditions	Yield
With water; potassium hydroxide for 16h; Inert atmosphere;	90%

2-amino-6-cyanobenzthiazole (19759-66-1) → 4-amino-3-mercaptobenzoic acid (14543-45-4)

Conditions	Yield
With sodium hydroxide for 72h; Heating;	76%

2-aminobenzothiazole-6-carboxylic acid (93-85-6) → 4-amino-3-mercaptobenzoic acid (14543-45-4)

Conditions	Yield
Stage #1: 2-aminobenzothiazole-6-carboxylic acid With water; potassium hydroxide for 24h; Inert atmosphere; Reflux; Stage #2: With hydrogenchloride In water Cooling with ice;	67.9%
Stage #1: 2-aminobenzothiazole-6-carboxylic acid With water; potassium hydroxide for 24h; Inert atmosphere; Reflux; Stage #2: With hydrogenchloride In water Cooling with ice;	67.9%
With potassium hydroxide In water for 24h; Inert atmosphere; Reflux;	67.9%
With water; potassium hydroxide for 3h; Reflux;	66.1%
With potassium hydroxide In water

2-aminobenzothiazole-6-carboxylic acid hydrochloride → 4-amino-3-mercaptobenzoic acid (14543-45-4)

Conditions	Yield
With potassium hydroxide for 4h; Heating;
With potassium hydroxide In water for 4h; Heating;

2-amino-benzothiazole-carboxylic acid-(6) → 4-amino-3-mercaptobenzoic acid (14543-45-4)

Conditions	Yield
With potassium hydroxide

4-Aminobenzonitrile (873-74-5) + [(Xantphos)2Pd(η3-CH2Ph]OTf → 4-amino-3-mercaptobenzoic acid (14543-45-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 82 percent / Br2; AcOH / 3 h / 20 °C 2: 76 percent / aq. NaOH / 72 h / Heating View Scheme

4-amino-benzoic acid (150-13-0) → 4-amino-3-mercaptobenzoic acid (14543-45-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: bromine / methanol / 2 h / -5 °C 2: hydrochloric acid / H2O / 0.5 h / Heating 3: potassium hydroxide / H2O / 4 h / Heating View Scheme

ethyl 2-aminobenzothiazole-6-carboxylate (50850-93-6) → 4-amino-3-mercaptobenzoic acid (14543-45-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1N aq. HCl / Heating 2: KOH / 4 h / Heating View Scheme

p-aminoethylbenzoate (94-09-7) → 4-amino-3-mercaptobenzoic acid (14543-45-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: Br2 / methanol / 2 h / -5 °C 2: 1N aq. HCl / Heating 3: KOH / 4 h / Heating View Scheme

4-Aminobenzonitrile (873-74-5) → 4-amino-3-mercaptobenzoic acid (14543-45-4)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: acetic acid / 3.5 h / 20 °C / Cooling with ice 2.1: hydrogenchloride; water / 6 h / 100 °C 3.1: potassium hydroxide; water / 24 h / Inert atmosphere; Reflux 3.2: Cooling with ice View Scheme
Multi-step reaction with 3 steps 1: acetic acid; bromine / 3.5 h / 20 °C / Cooling with ice 2: hydrogenchloride / water / 6 h / 100 °C 3: potassium hydroxide / water / 24 h / Inert atmosphere; Reflux View Scheme

4-amino-3-thiocyanatobenzonitrile (68867-21-0) → 4-amino-3-mercaptobenzoic acid (14543-45-4)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: hydrogenchloride; water / 6 h / 100 °C 2.1: potassium hydroxide; water / 24 h / Inert atmosphere; Reflux 2.2: Cooling with ice View Scheme
Multi-step reaction with 2 steps 1: hydrogenchloride / water / 6 h / 100 °C 2: potassium hydroxide / water / 24 h / Inert atmosphere; Reflux View Scheme

4-amino-3-mercaptobenzoic acid (14543-45-4) + bis(trichloromethyl) carbonate (32315-10-9) → 2-oxo-2,3-dihydro-1,3-benzothiazole-6-carboxylic acid (99615-68-6)

Conditions	Yield
Stage #1: 4-amino-3-mercaptobenzoic acid With potassium carbonate In tetrahydrofuran at 20℃; for 0.5h; Stage #2: bis(trichloromethyl) carbonate In tetrahydrofuran at -78℃; for 1h;	95%

4-amino-3-mercaptobenzoic acid (14543-45-4) + 4-nitrobenzaldehdye (555-16-8) → 2-(4-nitrophenyl)-1,3-benzothiazole-6-carboxylic acid (65644-51-1)

Conditions	Yield
With oxygen In ethanol	90%
In nitrobenzene for 6h; Heating;	55%

4-amino-3-mercaptobenzoic acid (14543-45-4) + thioacetamide (62-55-5) → 2-methyl-1,3-benzothiazole-6-carboxylic acid (6941-28-2)

Conditions	Yield
With hydrogenchloride In ethylene glycol Heating;	90%
With hydrogenchloride In water; ethylene glycol at 100℃; for 7h;	78%

4-amino-3-mercaptobenzoic acid (14543-45-4) + 2-phenoxyethanethioamide (35370-80-0) → 2-Phenoxymethyl-benzothiazole-6-carboxylic acid

Conditions	Yield
With hydrogenchloride In ethylene glycol Heating;	85%

4-amino-3-mercaptobenzoic acid (14543-45-4) + isopropenylbenzene (98-83-9) → 3-methyl-3-phenyl-3,4-dihydro-2H-benzo[b][1,4]thiazine-7-carboxylic acid

Conditions	Yield
With dipotassium peroxodisulfate; sodium iodide In acetonitrile at 80℃; for 16h; regioselective reaction;	84%

4-amino-3-mercaptobenzoic acid (14543-45-4) + methyl chloroformate (79-22-1) → 2-oxo-2,3-dihydro-1,3-benzothiazole-6-carboxylic acid (99615-68-6)

Conditions	Yield
Stage #1: 4-amino-3-mercaptobenzoic acid With sodium carbonate In water at 45℃; Inert atmosphere; Stage #2: methyl chloroformate In water at 45 - 80℃; Stage #3: With hydrogenchloride In water pH=2 - 3;	82.2%
Stage #1: 4-amino-3-mercaptobenzoic acid; methyl chloroformate With sodium carbonate In water at 80℃; Inert atmosphere; Stage #2: In water pH=2 - 3; Cooling with ice; Acidic conditions;	82.2%
With sodium carbonate In water at 45 - 80℃; Inert atmosphere;	82.2%

5-nitro-2-thiophenecarboxaldehyde (4521-33-9) + 4-amino-3-mercaptobenzoic acid (14543-45-4) → 2-(5-nitro-2-thienyl)-1,3-benzothiazole-6-carboxylic acid

Conditions	Yield
In nitrobenzene for 6h; Heating;	81%

4-amino-3-mercaptobenzoic acid (14543-45-4) + 4-dimethylamino-benzaldehyde (100-10-7) → 2-(4-Dimethylamino-phenyl)-benzothiazole-6-carboxylic acid

Conditions	Yield
With oxygen In ethanol	80%

4-amino-3-mercaptobenzoic acid (14543-45-4) + 4-methoxymethylbenzothioamide (653568-68-4) → 2-(4-methoxymethyl-phenyl)-benzothiazole-6-carboxylic acid (723316-68-5)

Conditions	Yield
With hydrogenchloride In 1-methyl-pyrrolidin-2-one for 8h; Heating;	80%

4-amino-3-mercaptobenzoic acid (14543-45-4) + 4-methoxy-benzaldehyde (123-11-5) → 2-(4-methoxyphenyl)-1,3-benzothiazole-6-carboxylic acid

Conditions	Yield
In nitrobenzene for 6h; Heating;	79%
With oxygen In ethanol	65%

4-amino-3-mercaptobenzoic acid (14543-45-4) + ortho-anisaldehyde (135-02-4) → 2-(2-methoxyphenyl)-1,3-benzothiazole-6-carboxylic acid

Conditions	Yield
In nitrobenzene for 6h; Heating;	79%

4-amino-3-mercaptobenzoic acid (14543-45-4) + 2-benzoyloxythioacetamide (40516-65-2) → 2-benzoyloxymethyl-benzothiazole-6-carboxylic acid (351465-00-4)

Conditions	Yield
With hydrogenchloride In ethylene glycol at 100℃; for 8h;	75%

5-nitrofurane-2-carboxaldehyde (698-63-5) + 4-amino-3-mercaptobenzoic acid (14543-45-4) → 2-(5-nitro-2-furyl)-1,3-benzothiazole-6-carboxylic acid

Conditions	Yield
In nitrobenzene for 6h; Heating;	73%

4-amino-3-mercaptobenzoic acid (14543-45-4) + 3-methoxy-benzaldehyde (591-31-1) → 2-(3-methoxyphenyl)-1,3-benzothiazole-6-carboxylic acid

Conditions	Yield
In nitrobenzene for 6h; Heating;	73%

4-amino-3-mercaptobenzoic acid (14543-45-4) + 4-hydroxy-benzaldehyde (123-08-0) → 2-(4-hydroxyphenyl)benzo[d]thiazole-6-carboxylic acid

Conditions	Yield
With oxygen In ethanol	65%

4-amino-3-mercaptobenzoic acid (14543-45-4) + benzaldehyde (100-52-7) → 2-phenyl-1,3-benzothiazole-6-carboxylic acid (19989-69-6)

Conditions	Yield
With oxygen In ethanol	60%

4-amino-3-mercaptobenzoic acid (14543-45-4) + 2,4-dinitrobenzaldehyde (528-75-6) → 2-(2,4-dinitrophenyl)-1,3-benzothiazole-6-carboxylic acid

Conditions	Yield
In nitrobenzene for 6h; Heating;	56%

methanol (67-56-1) + 4-amino-3-mercaptobenzoic acid (14543-45-4) → dimethyl 3,3'-disulfanediylbis(4-aminobenzoate) (93015-74-8)

Conditions	Yield
With sulfuric acid for 8h; Reflux;	52.2%

4-amino-3-mercaptobenzoic acid (14543-45-4) + 2-nitro-benzaldehyde (552-89-6) → 2-(2-nitrophenyl)-1,3-benzothiazole-6-carboxylic acid

Conditions	Yield
In nitrobenzene for 6h; Heating;	45%
In nitrobenzene Reflux;	20%

4-chlorosalicylaldehyde (2420-26-0) + 4-amino-3-mercaptobenzoic acid (14543-45-4) → 2-(4-chloro-2-hydroxyphenyl)-1,3-benzothiazole-6-carboxylic acid

Conditions	Yield
In nitrobenzene at 185℃; for 0.25h; Heating / reflux;	44%

4-amino-3-mercaptobenzoic acid (14543-45-4) + 3-nitro-benzaldehyde (99-61-6) → 2-(3-nitrophenyl)-1,3-benzothiazole-6-carboxylic acid

Conditions	Yield
In nitrobenzene for 6h; Heating;	43%

4-amino-3-mercaptobenzoic acid (14543-45-4) + 3,3-bis(methylthio)-2-(4-trifluoromethylpyrimidin-2-yl)acrylonitrile (1219483-62-1) → 2-[6-carboxybenzothiazol-2(3H)-ylidene]-2-(4-trifluoromethyl-pyrimidin-2-yl)acetonitrile (1219483-86-9)

Conditions	Yield
With dmap; potassium carbonate In ethanol at 160℃; for 0.4h; Microwave;	40%

4-amino-3-mercaptobenzoic acid (14543-45-4) + 4-nitro-benzoyl chloride (122-04-3) → 2-(4-nitrophenyl)-1,3-benzothiazole-6-carboxylic acid (65644-51-1)

Conditions	Yield
With pyridine

4-amino-3-mercaptobenzoic acid (14543-45-4) + 2-cyclohexylidenecyclohexanone (1011-12-7) → 1',3',4',11'a-tetrahydro-2'H-spiro[cyclohexane-1,11'-dibenzo[b,e][1,4]thiazepine]-8'-carboxylic acid

4-amino-3-mercaptobenzoic acid (14543-45-4) + 2,3-dichloroquinoxaline (2213-63-0) → 12H-benzo[5,6][1,4]thiazino[2,3-b]quinoxaline-3-carboxylic acid (19843-53-9)

4-amino-3-mercaptobenzoic acid (14543-45-4) + 2,3-dichloro-6-methylquinoxaline (39267-05-5) → 8-methyl-12H-benzo[5,6][1,4]thiazino[2,3-b]quinoxaline-3-carboxylic acid (31639-75-5)

Conditions	Yield
In ethanol Heating;

Upstream product

• 19759-66-1 2-amino-6-cyanobenzthiazole 
• 18330-64-8 4-amino-3-thiocyanatobenzoic acid 
• 873-74-5 4-Aminobenzonitrile 
• 66947-92-0 2-aminobenzo[d]thiazole-6-carboxylic acid methyl ester 
• 68867-21-0 4-amino-3-thiocyanatobenzonitrile 
• 93-85-6 2-aminobenzothiazole-6-carboxylic acid 
• 94-09-7 p-aminoethylbenzoate 
• 50850-93-6 ethyl 2-aminobenzothiazole-6-carboxylate 
• 150-13-0 4-amino-benzoic acid 
• 18330-76-2 2-aminobenzothiazole-6-carboxylic acid hydrochloride 

Downstream Products

• 19989-69-6 2-phenyl-1,3-benzothiazole-6-carboxylic acid 
• 6941-28-2 2-methyl-1,3-benzothiazole-6-carboxylic acid 
• 875846-26-7 2-(4-nitrophenyl)benzothiazole-6-carbonyl chloride 
• 95-22-7 4-(6-methyl-[2,6']bibenzothiazolyl-2'-yl)-aniline 
• 855266-37-4 6-methyl-2'-(4-nitro-phenyl)-[2,6']bibenzothiazolyl 
• 73302-00-8 4-(6-methyl-[2,6';2',6'']terbenzothiazol-2''-yl)-aniline 
• 1221408-57-6 N-{4-[4-(2-methoxyphenyl)piperazinyl]butyl}benzothiazolin-2-one-6-carboxamide 
• 93015-74-8 dimethyl 3,3'-disulfanediylbis(4-aminobenzoate) 
• 99615-68-6 2-oxo-2,3-dihydro-1,3-benzothiazole-6-carboxylic acid 
• 13127-94-1 2-(4-aminophenyl)benzo[d]thiazole-6-carboxylic acid 
• 351465-01-5 2-hydroxymethyl-benzothiazole-6-carboxylic acid 

Relevant academic research and scientific papers

Compound with dopamine D3 receptor adjusting activity, and applications thereof

The invention relates to a compound with dopamine D3 receptor adjusting activity, and applications thereof, and more specifically discloses dopamine receptor D3R as a novel target of post-traumatic stress disorder (PTSD) in prevention, treatment/or auxiliary treatment of PTSD, and screening of anti-PTSD medicines, and relates to applications of a compound with dopamine receptor D3R adjusting activity in preparation of medicines used for preventing, treatment and/or auxiliary treatment of PTSD.

NOVEL 2-AMINO-PYRIDINE AND 2-AMINO-PYRIMIDINE DERIVATIVES AND MEDICINAL USE THEREOF

Provided is a compound superior in an autotaxin inhibitory action and the like, effective as a prophylactic or therapeutic drug for diseases involving ATX. The present invention relates to a compound represented by the following formula (I): [wherein each symbol is as described in the DESCRIPTION], which has a superior autotaxin inhibitory action and is useful as a prophylactic or therapeutic drug for diseases involving ATX.

ANTI-INFECTIVE HETEROCYCLIC COMPOUNDS AND USES THEREOF

The present invention relates to heterocyclic compounds of Formula I useful as anti-infective agents. The present invention further relates to a method of treating an infection by administering such compounds, and to pharmaceutical compositions comprising such compounds.

NOVEL DOPAMINE D3 RECEPTOR LIGANDS, THE PREPARATION AND USE THEREOF

The invention discloses novel piperazine derivatives represented by formula I having activity for modulating dopamine D3 receptor, their stereoisomers, pharmaceutical salts, solvates, and the pharmaceutical compositions containing such compounds, their preparation and the use of such compounds for preventing or treating the diseases correlated with central nervous system disorder, such as Parkinson's disease, schizophrenia, drug addiction and relapse and the like, as well as the use of such compounds for kidney protection and immune modulation, or as implemental medicine for researching the function of D3R and the diseases correlated with disorder of D3R function.

NOVEL DOPAMINE D3 RECEPTOR LIGANDS AND PREPARATION AND MEDICAL USES OF THE SAME

The present invention relates to a novel piperazine derivative represented by Formula I having an activity for regulating dopamine D3 receptor, stereoisomers thereof, pharmaceutically acceptable salts or solvates, and a pharmaceutical composition comprising the compound, a process for preparing the same, and use thereof in the prevention or treatment of a disease associated with central nervous system dysfunction, such as Parkinson''s disease, schizophrenia, drug addiction and relapse, as well as kidney protection and immunoregulation, or as a tool for researching D3R function or diseases associated with D3R dysfunction.

A convenient route to 2-substituted benzothiazole-6-carboxylic acids using nitrobenzene as oxidant

Various substituted benzothiazole-6-carboxylic acids (4a-i) have been prepared by the condensation of 4-amino-3-mercaptobenzoic acid and aldehydes in nitrobenzene as oxidant. Compound 4i was found to be a good candidate as an inhibitor of ss-hematin formation in vitro.

COMPOUND INHIBITING DIPEPTIDYL PEPTIDASE IV

The invention aims to provide a dipeptidyl peptidase IV inhibitor which is satisfactory in respect of activity, stability and safety and has an excellent action as a pharmaceutical agent. The invention is directed to a compound represented by the following general formula or a pharmaceutically acceptable salt thereof: wherein R1 and R2 each represents hydrogen, an optionally substituted C1-6 alkyl group, or -COOR5 whereupon R5 represents hydrogen or an optionally substituted C1-6 alkyl group, or R1 and R2, together with a carbon atom to which they are bound, represent a 3- to 6-membered cycloalkyl group, R3 represents hydrogen or an optionally substituted C6-10 aryl group, R4 represents a hydrogen or a cyano group, D represents -CONR6-, -CO- or -NR6CO-, R6 represents hydrogen or an optionally substituted C1-6 alkyl group, E represents -(CH2)m- whereupon m is an integer of 1 to 3, -CH2OCH2-, or -SCH2-, n is an integer of 0 to 3, and A represents an optionally substituted bicyclic heterocyclic group or bicyclic hydrocarbon group.

Antirheumatic agents: Novel methotrexate derivatives bearing a benzoxazine or benzothiazine moiety

Novel methotrexate (MTX) derivatives bearing dihydro-2H-1,4- benzothiazine or dihydro-2H-1,4-benzoxazine were synthesized and tested for in vitro antiproliferative activities against human synovial cells (hSC) and human peripheral blood mononuclear cells (hPBMC) obtained from patients with rheumatoid arthritis and healthy volunteers, respectively. In vivo antiarthritic activities of these derivatives were also evaluated in a rat adjuvant arthritis model. N-[[4-[(2,4-Diaminopteridin-6-yl)methyl]-3,4- dihydro-2H-1,4-benzothiazin-7-yl]carbonyl]-L-glutamic acid (3c) exhibited more potent antiproliferative activities in hSC and hPBMC than MTX in vitro. Antiproliferative activities of N-[[4-[(2,4-diaminopteridin-6-yl)methyl]- 3,4-dihydro-2H-1,4-benzoxazin-7-yl]carbonyl]-L-homoglutamic acid (3b) and N- [[4-[(2,4-diaminopteridin-6-yl)methyl]-3,4-dihydro-2H-1,4-benzothiazin-7- yl]carbonyl]-L-homoglutamic acid (3d) (MX-68) were comparable to that of MTX in these in vitro assays. Compounds 3b,d (MX-68) significantly suppressed progression of the adjuvant arthritis in a dose-dependent manner ranging from 0.5 to 2.5 mg/kg (po). In addition, 3d (MX-68) completely suppressed this progression at the dose of 2.5 mg/kg (po). Importantly, 3d (MX-68) having benzothiazine and homoglutamate, as expected, did not undergo polyglutamation, a process which may be responsible for the associated side effects of MTX. These results suggest that 3d (MX-68) is a potent and safe candidate antirheumatic agent, absent of the side effects of MTX.

10,11-Dihydrodibenzo[b,f][1,4]thiazepine carboxylic acids esters and amides thereof

Novel dibenzo[b,f][1,4]thiazepine derivatives are employed in the treatment and control of allergic conditions such as allergic asthma.