5790-69-2

Usage

Uses

Used in Pharmaceutical Industry:
2-Amino-5-chlorobenzenesulfonamide is utilized as an antibacterial agent for the treatment of urinary tract infections. It functions by inhibiting the growth of bacteria, and its efficacy is often enhanced when combined with other antibiotics to achieve a synergistic effect.
Used in Dye Production:
In the past, 2-Amino-5-chlorobenzenesulfonamide has been employed in the production of dyes, capitalizing on its chemical properties to create a range of colorants for various applications.
Used in Medication Composition:
Sulfanilamide has also been incorporated as a component in some medications, contributing to their therapeutic effects.
However, it is important to note that the use of 2-Amino-5-chlorobenzenesulfonamide has diminished over time due to the advent of more potent and less toxic antibiotics. Additionally, special care must be taken in handling this chemical, as it is harmful if ingested, inhaled, or absorbed through the skin, and it can cause eye and skin irritation.

InChI:InChI=1/C6H7ClN2O2S/c7-4-1-2-5(8)6(3-4)12(9,10)11/h1-3H,8H2,(H2,9,10,11)

Upstream product

• 5800-59-9 7-chloro-2,3-dihydro-3-oxo-4H-1,2,4-benzothiadiazine 
• 3306-62-5 2-AMINOBENZENESULFONAMIDE 
• 68379-05-5 5-chloro-2-nitrobenzenesulfonamide 
• 21792-87-0 5-chloro-2-nitrobenzenesulfonyl chloride 
• 1635-61-6 5-chloro-2-nitroaniline 
• 17800-60-1 2-acetylamino-benzenesulfonic acid acetylamide 
• 181428-37-5 C₇H₆Cl₂N₂O₃S 
• 106-47-8 4-chloro-aniline 
• 90794-87-9 4-Chlor-2-acetylsulfamoyl-acetanilid 

Downstream Products

• 93899-88-8 7-chloro-3-phenethyl-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine 1,1-dioxide 
• 51138-83-1 2-Amino-5-chlor-benzolsulfonyl-cyanamid-Na-Salz 
• 92294-64-9 7-chloro-3-cyclohex-2-enylmethyl-3,4-dihydro-2H-benzo[1,2,4]thiadiazine 1,1-dioxide 
• 51138-82-0 benzyl-(7-chloro-1,1-dioxo-1,2(4)-dihydro-1λ⁶-benzo[1,2,4]thiadiazin-3-yl)-amine 
• 94712-09-1 7-chloro-3-(3,4-diethoxy-phenyl)-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine 1,1-dioxide 
• 3966-97-0 3-benzyl-7-chloro-2H-benzo[e][1,2,4]thiadiazine 1,1-dioxide 
• 93187-23-6 7-chloro-3-cyclohexyl-2⁽⁴⁾H-benzo[1,2,4]thiadiazine 1,1-dioxide 
• 93309-25-2 7-chloro-3-phenoxymethyl-2H-benzo[e][1,2,4]thiadiazine 1,1-dioxide 
• 54734-82-6 2-amino-5-chloro-3-iodobenzenesulfonamide 
• 22503-72-6 IDRA 21 
• 92629-15-7 4-Chloro-2-sulfamoylcrotonoylanilide 
• 101064-10-2 N-(4-chloro-2-sulfamoyl-phenyl)-succinamic acid methyl ester 
• 364-98-7 diazoxide 
• 93867-16-4 3-Dimethylanilino-7-chlor-3,4-dihydro-1,2,4-benzothiadiazin-1,1-dioxid 

Relevant academic research and scientific papers

Method for preparing diazoxide

The invention discloses a method for preparing diazoxide. The method comprises the following steps: reacting o-aminobenzenesulfonamide with N-chlorosuccinimide in a chlorine solvent to obtain 2-amino-5-chlorobenzenesulfonamide, mixing the 2-amino-5-chlorobenzenesulfonamide, an imidazolium salt and an amide solvent, and heating the obtained mixture to react to obtain the diazoxide; or mixing o-aminobenzenesulfonamide, the imidazolium salt and the amide solvent, heating for a reaction to obtain a compound IV, and reacting the compound IV with N-chlorosuccinimide in the chlorine solvent so as toobtain the diazoxide. The invention also discloses an application of imidazole hydrochloride as a catalyst in the preparation of diazoxide. The method avoids the problems that chlorosulfonyl isocyanate and strong acid (sulfuric acid) which have high corrosivity and toxicity are used in the reaction process and the reaction temperature is high (240-250 DEG C), and the reaction steps are short; thetotal yield of the two steps can reach 90% or above; and compared with publicly reported diazoxide preparation methods, the synthesis method of the invention overcomes numerous defects, so that the synthesis method is suitable for industrial production.

Synthetic method of diazoxide

The invention relates to a synthetic method of diazoxide (I). The synthetic method comprises the following steps of (a) carrying out catalytic hydrogenation reduction on 5-chlorine-2-nitrobenzenesulfonamide (II) in a solvent A through raney nickel so as to obtain 5-chlorine-2-aminobenzenesul fonamide (III), wherein the reduction reaction temperature ranges from 20 to 40 DEG C, the reduction reaction pressure ranges from 3 to 10kg/cm, and the reduction reaction time ranges from 3 to 5 hours; (b) acetylizing the 5-chlorine-2-aminobenzenesul fonamide (III) in a solvent B through an acylation reagent with the existence of an inorganic substance acid-binding agent, carrying out ring-closure reaction on a product in a high-boiling-point inert solvent C, and obtaining a diazoxide (I) crude product, wherein the acetylation reaction temperature ranges from 0 to 30 DEG C, the acetylation time ranges from 2 to 10 hours, the ring-closure reaction temperature ranges from 240 to 250 DEG C, and the ring-closure reaction time ranges from 0.5 to 1.5 hours; (c) refining the diazoxide (I) crude product through ethyl alcohol with the concentration being 80 percent, and obtaining a diazoxide (I) finished product.

COMPOSITIONS AND METHODS FOR THE TREATMENT OF METABOLIC SYNDROME

The invention relates to the compounds of formula I or its pharmaceutical acceptable salts, as well as polymorphs, solvates, enantiomers, stereoisomers and hydrates thereof. The pharmaceutical compositions comprising an effective amount of compounds of fo

Synthesis and pharmacological activity of N-(2,2-dimethyl-3,4-dihydro-2H-1- benzopyran-4-yl)-4H-1,2,4-benzothiadiazine-3-carboxamides 1,1-dioxides on rat uterus, rat aorta and rat pancreatic β-cells

N-(2,2-Dimethyl-3,4-dihydro-2H-1-benzopyran-4-yl)-4H-1,2, 4-benzothiadiazine-3-carboxamides 1,1-dioxides were prepared and evaluated on rat uterus, rat aortic rings and rat pancreatic β-cells. Pharmacological studies conducted on rat uterus indicated that several of these original hybrid compounds displayed a strong myorelaxant activity. The most active compounds hold a bromine atom at the 6-position of the dihydrobenzopyran ring. Moreover, the compounds failed to display a marked inhibitory effect on insulin secretion and vascular myogenic activity. These features suggest that the 6-bromo compounds could be relatively selective towards the uterine smooth muscle.

Acetic acid derivatives of 3,4-dihydro-2 H-1,2,4-benzothiadiazine 1,1-dioxide as a novel class of potent aldose reductase inhibitors

A series of novel benzothiadiazine 1,1-dioxide derivatives were synthesized and tested for their inhibitory activity against aldose reductase. Of these derivatives, 17 compounds, having a substituted N2-benzyl group and a N4-acetic acid group on the benzothiadiazine, were found to be potent and selective aldose reductase inhibitors in vitro with IC50 values ranging from 0.032 to 0.975 μM. 9m proved to be the most active in vitro. The eight top-scoring compounds coming from the in vitro test for ALR2 inhibition activity were then tested in vivo, whereby three derivatives, 9i, 9j, and 9m, demonstrated a significantly preventive effect on sorbitol accumulation in the sciatic nerve in the 5-day streptozotocin-induced diabetic rats in vivo. Structure-activity relationship and molecular docking studies highlighted the importance of substitution features of N4-acetic acid group and halogen-substituted N2-benzyl group in the benzothiadiazine scaffold and indicated that substitution with hallogen at C-7 had a remarkably strong effect on ALR2 inhibition potency.

Substituted benzothiadizine inhibitors of Hepatitis C virus polymerase

The synthesis and optimisation of HCV NS5B polymerase inhibitors with improved potency versus the existing compound 1 is described. Substitution in the benzothiadiazine portion of the molecule, furnishing improvement in potency in the high protein Replicon assay, is highlighted, culminating in the discovery of 12h, a highly potent oxyacetamide derivative.

Design, synthesis, and SAR of cis-1,2-diaminocyclohexane derivatives as potent factor Xa inhibitors. Part II: Exploration of 6-6 fused rings as alternative S1 moieties

A series of cis-1,2-diaminocyclohexane derivatives possessing a 6-6 fused ring for the S1 moiety were synthesized as novel factor Xa (fXa) inhibitors. The synthesis, structure-activity relationship (SAR), and physicochemical properties are reported herein, together with the discovery of compound 45c, which has potent anti-fXa activity, good physicochemical properties and pharmacokinetic (PK) profiles, including a reduced negative food effect.

Synthesis and pharmacological evaluation of 1,2,4-benzothiadiazin-1,1- dioxides bearing 5- or 7-sulfonylurea moieties

A series of substituted benzothiadiazin-1,1-dioxides bearing sulfonylurea moieties in position 5 or 7 has been synthesized. The most powerful vasodilator compound was 18a, obtained by substitution of a sulfonylurea moiety on position 7 of the diazoxide skeleton by means of a SO2 group. Interestingly, 18a and 18b were found inactive on insulin secretion at 50 μM and likely devoid of adverse effect on glycemia, suggesting a special therapeutic potential for these compounds.

5'-alkyl-benzothiadiazides: a new subgroup of AMPA receptor modulators with improved affinity.

AMPA receptors form a major subdivision of the glutamate receptor family that mediates excitatory synaptic transmission in the brain. Currents through AMPA receptors can be up- or down-regulated by compounds that allosterically modulate receptor kinetics through binding sites distinct from that for glutamate. One of those modulators is the benzothiadiazide IDRA-21 which has been reported to enhance synaptic transmission and be effective in behavioral tests, but typically requires threshold concentrations of at least 100 microM to be active in vitro. In this study, new benzothiadiazides were developed with IDRA-21 as lead compound and examined for their potency in modulating AMPA receptor kinetics. A significant increase in drug affinity was obtained by alkyl substitution at the 5'-position of IDRA-21; substitutions at other positions of the benzothiadiazide core generally did not yield a further gain in affinity and in some cases abolished drug binding. The 5'-ethyl derivative exhibited an EC(50) value in the order of 22 microM which represents about a 30-fold gain in affinity over that of IDRA-21. The EC(50) value is comparable to that of cyclothiazide, the most potent benzothiadiazide drug, but the effects on AMPA receptors differed substantially between these two compounds in that the 5'-ethyl derivative of IDRA-21 greatly increased the binding affinity for receptor agonists whereas cyclothiazide is known to reduce agonist binding. The structure--activity relationships reported here thus offer to provide new insights how receptor kinetics is linked to particular aspects of receptor--drug interactions.