- The X-ray Structures of 2,4-Dibromothiazole and 2,4-Diacetyl-5-bromothiazole
-
2,4-Dibromothiazole [orthorhombic, a = 6.700 (10), b = 16.21 (3), c = 5.516 (8) ?, space group Fmm2] shows a disordered crystal structure with molecules randomly oriented with respect to the direction of the Br-C(2)-N-C(2)-Br unit and the remaining ring atoms S(3) and C(3)H showing mixed occupancy. 2,4-Diacetyl-5-bromothiazole [triclinic, a = 4.040 (2), b = 8.254 (5), c = 13.208 (8) ?, α = 96.191 (17), β = 93.865 (16), γ = 94.067 (11)°, space group P-1] shows a structure dominated by halogen bonding, intramolecular between 4-COMe and 5-Br and intermolecular between 2-COMe of one molecule and 5-Br of the next. Graphical Abstract: 2,4-Dibromothiazole is disordered in the crystal structure with molecules randomly oriented either way round as shown. There is evidence for unusual intramolecular, and perhaps also intermolecular, halogen bonding between Br and C = O in the structure of 2,4-diacetyl-5-bromothiazole.[Figure not available: see fulltext.]
- Aitken, Kati M.,Aitken, R. Alan,MacGregor, Callum I.,Traore, Mohamed D. M.,Slawin, Alexandra M. Z.
-
-
Read Online
- Pyrrolo[2,3-d:5,4-d′]bisthiazoles: Alternate Synthetic Routes and a Comparative Study to Analogous Fused-Ring Bithiophenes
-
New synthetic methods have been developed for the preparation of 4-alkyl- and 4-aryl-pyrrolo[2,3-d:5,4-d′]bisthiazole (PBTz) building blocks from 2,4-thiazolidinedione. The resulting PBTz products have been fully characterized via structural, electronic, and optical methods, thus allowing full comparison to the previously reported dithieno[3,2-b:2′,3′-d]pyrrole (DTP) analogues. Such comparisons then allow a detailed discussion of the relative electronic effects of the various methods utilized to tune the properties of the parent DTP building block.
- Uzelac, Eric J.,McCausland, Casey B.,Rasmussen, Seth C.
-
-
Read Online
- Synthesis, molecular docking, antimicrobial, antioxidant and anticonvulsant assessment of novel S and C-linker thiazole derivatives
-
In medicinal chemistry, the searching for new anticonvulsants with greater selectivity and reduced toxicity is still active. Therefore, multistep reaction sequence has been explored to obtained novel series of S and C-linker thiazole derivatives (7a-h and 8a-d). The final compounds were screened for antimicrobial activity against different microbial strains. The DPPH and hydroxyl radical scavenging methods were evaluated to assess their antioxidant capabilities. The anticonvulsant activity was established in MES and PTZ seizure models and the most active compound was 7b and 7 g which showed 100% protection. A computational study was also carried out including drug likeness and docking studies.
- Alsalme, Ali,Krishnaiah, Prakash,Kumar, K. Yogesh,Prasad, S. B. Benaka,Prashanth, M. K.,Raghu, M. S.,Raveesha, R.
-
-
- Composite tetraheteroarylenes and related higher cyclic oligomers of heteroarenes produced by palladium-catalyzed direct coupling
-
Substantial research interests have been focused on cyclic π-conjugated molecules owing to their unique chemical and physical properties. By constructing hybrid aromatic arrays within these cyclic systems, new series of composite macrocycles would be prov
- Fukuzumi, Keita,Nishii, Yu Ji,Miura, Masahiro
-
p. 2030 - 2037
(2019/12/23)
-
- Novel 4,8-benzobisthiazole copolymers and their field-effect transistor and photovoltaic applications
-
A series of copolymers containing the benzo[1,2-d:4,5-d′]bis(thiazole) (BBT) unit has been designed and synthesised with bisthienyl-diketopyrrolopyrrole (DPP), dithienopyrrole (DTP), benzothiadiazole (BT), benzodithiophene (BDT) or 4,4′-dialkoxybithiazole (BTz) comonomers. The resulting polymers possess a conjugation pathway that is orthogonal to the more usual substitution pathway through the 2,6-positions of the BBT unit, facilitating intramolecular non-covalent interactions between strategically placed heteroatoms of neighbouring monomer units. Such interactions enable a control over the degree of planarity through altering their number and strength, in turn allowing for tuning of the band gap. The resulting 4,8-BBT materials gave enhanced mobility in p-type organic field-effect transistors of up to 2.16 × 10-2 cm2 V-1 s-1 for pDPP2ThBBT and good solar cell performance of up to 4.45% power conversion efficiency for pBT2ThBBT.
- Conboy, Gary,Taylor, Rupert G. D.,Findlay, Neil J.,Kanibolotsky, Alexander L.,Inigo, Anto R.,Ghosh, Sanjay S.,Ebenhoch, Bernd,Krishnan Jagadamma, Lethy,Thalluri, Gopala Krishna V. V.,Sajjad, Muhammad T.,Samuel, Ifor D. W.,Skabara, Peter J.
-
supporting information
p. 11927 - 11936
(2017/11/30)
-
- Synthesis of Brominated Thiazoles via Sequential Bromination-Debromination Methods
-
The synthesis of the full family of bromothiazoles has been revisited in order to update and optimize their production. The species reported include 2-bromothiazole, 4-bromothiazole, 5-bromothiazole, 2,4-dibromothiazole, 2,5-dibromothiazole, 4,5-dibromothiazole, and 2,4,5-tribromothiazole, the majority of which are produced via sequential bromination and debromination steps. This complete family can now be produced without the use of elemental bromine, and the presented methods have allowed the physical and NMR spectroscopic characterization of the full family to be reported for the first time.
- Uzelac, Eric J.,Rasmussen, Seth C.
-
p. 5947 - 5951
(2017/06/07)
-
- Pyrrole inhibitors of S-nitrosoglutathione reductase as therapeutic agents
-
The present invention is directed to inhibitors of S-nitrosoglutathione reductase (GSNOR), pharmaceutical compositions comprising such GSNOR inhibitors, and methods of making and using the same.
- -
-
Page/Page column 298-299
(2015/11/16)
-
- Convenient preparation of halo-1,3-thiazoles: Important building blocks for materials and pharmaceutical synthesis
-
Convenient, scalable and high-yielding approaches to 2,5- and 2,4-dibromo-1,3-thiazole are reported that offer significant improvements over previously reported approaches. 2,5-Dibromo-1,3-thiazole was generated in two steps from commercially inexpensive 2-amino-1,3-thiazole, whereas 2,4-dibromo-1,3-thiazole was generated in a single step from commercially inexpensive 1,3-thiazolidine-2,4-dione. As part of this study, convenient approaches to 2-bromo- and 2-iodo-1,3-thiazole were also developed. Georg Thieme Verlag Stuttgart · New York.
- Grubb, Alan M.,Schmidt, Michael J.,Seed, Alexander J.,Sampson, Paul
-
experimental part
p. 1026 - 1029
(2012/05/05)
-
- Discovery of potent and novel S-nitrosoglutathione reductase inhibitors devoid of cytochrome P450 activities
-
The pyrrole based N6022 was recently identified as a potent, selective, reversible, and efficacious S-nitrosoglutathione reductase (GSNOR) inhibitor and is currently undergoing clinical development for the treatment of acute asthma. GSNOR is a member of the alcohol dehydrogenase family (ADH) and regulates the levels of S-nitrosothiols (SNOs) through catabolism of S-nitrosoglutathione (GSNO). Reduced levels of GSNO, as well as other nitrosothiols (SNOs), have been implicated in the pathogenesis of many diseases including those of the respiratory, cardiovascular, and gastrointestinal systems. Preservation of endogenous SNOs through GSNOR inhibition presents a novel therapeutic approach with broad applicability. We describe here the synthesis and structure-activity relationships (SAR) of novel pyrrole based analogues of N6022 focusing on removal of cytochrome P450 inhibition activities. We identified potent and novel GSNOR inhibitors having reduced CYP inhibition activities and demonstrated efficacy in a mouse ovalbumin (OVA) model of asthma.
- Sun, Xicheng,Qiu, Jian,Strong, Sarah A.,Green, Louis S.,Wasley, Jan W.F.,Blonder, Joan P.,Colagiovanni, Dorothy B.,Mutka, Sarah C.,Stout, Adam M.,Richards, Jane P.,Rosenthal, Gary J.
-
supporting information; experimental part
p. 5849 - 5853
(2011/10/19)
-
- Compounds and Methods of Treatment
-
A derivative, which is useful as a ret kinase inhibitor is described herein. The described invention also includes methods of using the same in the treatment of diseases mediated by inappropriate ret kinase activity.
- -
-
Page/Page column 17
(2008/12/08)
-
- TRIAZOLOPYRAZINE COMPOUNDS USEFUL FOR THE TREATMENT OF DEGENERATIVE & INFLAMMATORY DISEASES
-
Novel [1.2.4]triazolo[1,5-a]pyrazine compounds are disclosed that have a formula represented by the following (formula I). The compounds may be prepared as pharmaceutical compositions, and may be used for the prevention and treatment of a variety of conditions in mammals including humans, including by way of non-limiting example, arthritis, inflammation, and others.
- -
-
Page/Page column 80
(2008/06/13)
-
- Amino-5-(5-membered)hetero-arylimidazolone compounds and the use thereof for beta-secretase modulation
-
The present invention provides a 2-amino-5-heteroaryl-5-phenylimidazolone compound of formula I The present invention also provides methods for the use thereof to inhibit β-secretase (BACE) and treat β-amyloid deposits and neurofibrillary tangles
- -
-
Page/Page column 21
(2008/06/13)
-
- Halogenated 2′-chlorobithiazoles via Pd-catalyzed cross-coupling reactions
-
Halogenated bithiazoles allow facile further functionalization and are, therefore, suitable intermediates for the synthesis of compounds with interesting biological activity or material science properties. The applicability of three coupling methods (Negi
- Stanetty, Peter,Schnuerch, Michael,Mihovilovic, Marko D.
-
p. 3754 - 3761
(2007/10/03)
-
- Reactivity of unsaturated sultones synthesized from unsaturated alcohols by ring-closing metathesis. Application to the racemic synthesis of the originally proposed structure of mycothiazole
-
Unsaturated sultones have been synthesized from various primary or secondary alkenols by ring-closing metathesis of the corresponding unsaturated sulfonates. By treatment with a strong base, β,γ-unsaturated sultones can be metalated and subsequently alkylated with electrophiles. When iodomethylmagnesium chloride was selected as the electrophile, seven-membered ring β,γ-unsaturated sultones were converted into homoallylic conjugated (Z)-dienols. This methodology was applied to the racemic synthesis of the originally proposed structure of the marine natural product mycothiazole.
- Le Flohic, Alexandre,Meyer, Christophe,Cossy, Janine
-
p. 9017 - 9037
(2007/10/03)
-
- P-38 inhibitors
-
Provided are 5-membered heterocycle-based p38 kinase, including p38α and p38β kinase, inhibitors. Pharmaceutical compositions containing the compounds are also provided. Methods of use of the compounds and compositions are also provided, including methods of treatment, prevention, or amelioration of one or more symptoms of p38 kinase mediated diseases and disorders, including, but not limited to, inflammatory diseases and disorders.
- -
-
-
- Azoles. Part 8. Metallation and Bromine -> Lithium Exchange Reactions of Polyhalogenothiazoles
-
2,4-Dichloro- and 2,4-dibromo-thiazole were deprotonated at position-5 with LiN(iPr)2 in THF at -78 deg C and the resulting lithium compound was quenched with various reagents, to yield various trisubstituted thiazoles. 2,5-Dibromo-4-chlorothiazole reacted with n-butyllithium in THF at -78 deg C at position-5 and the resulting lithium derivative gave 2-bromo-4-chloro-5-substituted thiazoles when quenched with the appropriate reagent.Both the 2- and 5-bromine-atoms were reactive in diethyl ether. 2,5-Dibromothiazole failed to deprotonate at position-4 under various reaction conditions, whereas treatment of 2,4,5-tribromothiazole with 1 mole equivalent of n-butyllithium in THF at -90 deg C, followed by addition of dimethyl disulfide after 30 min, gave a high yield of the 2,5-bis(methylthio)-compound.The tribromo-compound was also treated with 1 mole equivalent of n-butyllithium or methyllithium under various reaction conditions and the products formed after hydrolysis were analysed by 1H NMR spectroscopy.The 5-bromine-atom is the most reactive and greater selectivity is obtained with methyllithium.
- Athmani, Salah,Bruce, Andrew,Iddon, Brian
-
p. 215 - 219
(2007/10/02)
-
- 2-,4- OR 5-SUBSTITUTED THIAZOLE DERIVATIVES
-
Pharmaceutical compounds and compositions which may be represented by the following structural formulae: STR1 where R is hydrogen or lower alkyl and NR'" is amino, (C 1-C 6) alkylamino, dialkylamino, or trialkylamino, pyrrolidino or piperidino. The compounds are useful in treating central cholinergic disfunction in mammals. "
- -
-
-
