289-06-5

Usage

Uses

Used in Pharmaceutical Industry:
THIADIAZOLE is used as a bioisostere for the synthesis of antibiotics such as cephalosporine and cefazedone, which are widely used in the treatment of bacterial infections.
Used in Treatment of African Trypanosomes:
THIADIAZOLE is used as a base for the development of Megazole, a drug widely used in the treatment of African trypanosomes, also known as sleeping sickness.
Used in Cancer Treatment:
THIADIAZOLE is used as a component in the development of Azetepa, a phosphorus-containing drug used for the treatment of cancer.
Used in Agriculture:
THIADIAZOLE is used as a base for the development of Tebtheuron, a broad-spectrum herbicide used to control a variety of weeds and herbaceous and woody plants.
Used in Pest Control:
Numerous THIADIAZOLE derivatives are patented as bactericides, insecticides, and fungicides, used in the control and management of various pests in agriculture and other industries.

Chemical Reactivity

Atomic charges have been calculated by the DFT method. The maximum charge was found at the S atom (0.818) and thus it is the favorite position for soft nucleophilic attack. The atomic charge on each carbon is ?0.3275. Because of the presence of the two pyridine-like nitrogen atoms in the ring, which make the C2 - and C5 -positions electronically poor, nucleophilic substitution of the leaving groups present at either the C2 - or C5 -position becomes highly facile. However, the atomic charge on N3 and N4 (?0.0308) makes them preferential sites for electrophilic attack and readily N-alkylated or N-acylated. In strongly basic conditions the thiadiazole ring leads to ring fission.

Biological Activity

Anti-inflammatory,antivira and antimicrobial.

InChI:InChI=1/C2H2N2S/c1-3-4-2-5-1/h1-2H

Upstream product

• 61929-24-6 2-bromo-1,3,4-thiadiazole 
• 30962-16-4 potassium dithioformate 
• 18686-82-3 2-mercapto-1,3,4-thiadiazole 
• 628-36-4 diformylhydrazine 
• 110-89-4 piperidine 
• 1072-71-5 2,5-Dimercapto-1,3,4-thiadiazole 
• 109-89-7 diethylamine 
• 111-92-2 dibutylamine 
• 110-85-0 piperazine 
• 50-00-0 formaldehyd 

Downstream Products

• 27369-33-1 3-Benzyl-1,3,4-thiadiazolium-chlorid 
• 114395-39-0 3-(p-Bromphenacyl)-1,3,4-thiadiazolium-bromid 
• 851681-89-5 Oxindole 

Relevant academic research and scientific papers

Additive compound for curing halogenated polymers

The present invention relates to 1,3,4-thiadiazole reaction products useful as accelerators and/or curing agents for halogenated polymers in rubber vulcanization processes, and to halogenated polymer compositions containing the thiadiazole derivatives, as well as a method of preparing the same. The additive is the reaction product of a 1,3,4-thiadiazole compound and a dithiocarbamic acid or an amine, or an isomer thereof.

Thiadiazoles and oxadiazoles and their use as phosphodiesterase-7 inhibitors

The invention provides 1,3,4-thiadiazoles and 1,3,4-oxadiazoles having the following Formula I: in which, Y is S or O, R1 is alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, cycloalkenyl, aryl, heteroaryl or a polycyclic group, optionally substituted, R2 is alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, cycloalkenyl or aryl optionally substituted, R3 is X2—R′3, in which X2 is a binding group and R′3 is cycloalkyl, heterocycloalkyl, cycloalkenyl, aryl, heteroaryl, or a polycyclic group; optionally substituted, or their pharmaceutically acceptable derivatives, a compound of Formula I, for their preparation, and processes for pharmaceutical compositions containing methods of using the compounds for the treatment of disorders for which a treatment by a PDE7 inhibitor is relevant.

Heterocycle substituted purine derivatives as potent antiproliferative agents

The compounds of the present invention are 2,6,9-trisubstituted purine derivatives which are inhibitors of cyclin/cdk complexes. The compounds of the current invention also are potent inhibitors of human cellular proliferation. As such, the compounds of the present invention constitute pharmaceutical compositions with a pharmaceutically acceptable carrier. Such compounds are useful in treating a disorder mediated by elevated levels of cell proliferation in a mammal compared to a healthy mammal by administering to such mammal an effective amount of the compound. Examples of the compounds of the present invention are represented by the following chemical structures: with Y, V, A, R1, R2, R3, R4, R7, and n1 defined herein.

Trisubstituted heterocyclic compounds and their use as fungicides

Compounds of general formula (I): in which:Het represents a five or six membered saturated, partially unsaturated or aromatic ring containing between one and six heteroatoms of the group N, O, S, in which the heterocycle is substituted in an adjacent manner with -P-Q1-T-Q2, -GZ and Y, such that the substituant -GZ is adjacent to both. the other substituants being as defined in the description,process for preparing these compounds,fungicidal compositions comprising these compounds,processes for treating plants by applying these compounds or compositions.

Substituted amino methyl factor Xa inhibitors

The present application describes substituted-aminomethyl substituted compounds and derivatives thereof, or pharmaceutically acceptable salt forms thereof, which are useful as inhibitors of factor Xa.

Oxazole PPAR antagonist

A method is disclosed for rational design of a PPAR, FXR, LXR-alpha, or LXR-beta antagonist comprising chemical modification of a PPAR, FXR, LXR-alpha, or LXR-beta agonist to: a) prevent formation of a hydrogen bond between the agonist and tyrosine or histidine, or tryptophan involved in receptor activation; and/or b) displace the tyrosine or histidine, or tryptophan involved in receptor activation from its agonist bound position. Preferably, little or no additional changes are made in the structure of the agonist so that the resulting antagonist is a close structural analogue of the agonist. Specific examples of PPAR gamma antagonists designed and prepared using the method of this invention are compounds of Formula (I) or (II), or pharmaceutically acceptable salts or solvates thereof, where in Formula (I) X is O, S, or NH; and R is methyl, ethyl, n-propyl, i-propyl, cyclopropyl, n-butyl, phenyl, or —CH2OCH3and wherein in Formula (II) X is C or N; and R is methyl, ethyl, n-propyl, i-propyl, —CH2OCH3, or —CO2CH3.

Heteroaryl-phenyl substituted factor Xa inhibitors

The present application describes heteroaryl-phenyl substituted compounds and derivatives thereof, or pharmaceutically acceptable salt or prodrug forms thereof, which are useful as inhibitors of factor Xa.

Heteroaryl- phenyl heterobicyclic factor Xa inhibitors

The present application describes heteroaryl-phenyl heterobicycles and derivatives thereof, or pharmaceutically acceptable salt forms thereof, which are useful as inhibitors of factor Xa.

Benzimidazolinones, benzoxazolinones, benzopiperazinones, indanones, and derivatives thereof as inhibitors of factor Xa

The present application describes inhibitors of factor Xa of formula I: or pharmaceutically acceptable salt forms thereof, wherein W, W1, W2, and W3may be N or C and J, Ja, and Jbcombine to form a substituted carbocycle or heterocycle.

6-membered aromatics as factor Xa inhibitors

The present application describes 6-membered aromatics of formula I: or pharmaceutically acceptable salt forms thereof, wherein D may be CH2NH2 or C(=NH)NH2, which are useful as inhibitors of factor Xa.