- Efficient synthesis of 6,6a-dihydroisoindolo[2,1-a]quinazoline-5,11-dione derivatives catalyzed by functionalized nanoporous silica
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An efficient and facile method has been developed for the synthesis of various 6,6a-dihydroisoindolo[2,1-a]quinazoline-5,11-dione derivatives, via a three-component reaction of 2-amino-N-(R)-benzamide derivatives with 2-formylbenzoic acid using sulfonic acid functionalized nanoporous silica as an efficient catalyst in ethanol under reflux. High yield of the desired products, reusability of the catalyst, and effortless workup step without using chromatography are the advantages of this method. Graphic abstract: [Figure not available: see fulltext.]
- Rayatzadeh, Ayeh,Haghipour, Sirous
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p. 103 - 107
(2021/02/05)
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- Palladium-catalyzed atroposelective coupling-cyclization of 2-isocyanobenzamides to construct axially chiral 2-aryl- And 2,3-diarylquinazolinones
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A palladium-catalyzed imidoylative cycloamidation of N-alkyl-2-isocyanobenzamides with 2,6-disubstituted aryl iodides, affording unprecedented axially chiral 2-arylquinazolinones, has been developed with good yields and atroposelectivities. In this coupling-cyclization process, the biaryl linkage and the heteroaromatic ring are formed sequentially in one step. When N-(2,4dimethoxyphenyl)-2-isocyanobenzamide is applied as a substrate, 2,3-diarylquinazolinones containing two stereogenic axes are produced with moderate diastereoselectivity and good enantioselectivities.
- Teng, Fan,Yu, Ting,Peng, Yan,Hu, Weiming,Hu, Huaanzi,He, Yimiao,Luo, Shuang,Zhu, Qiang
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supporting information
p. 2722 - 2728
(2021/03/01)
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- Design, synthesis, in vitro and in silico biological assays of new quinazolinone-2-thio-metronidazole derivatives
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A new series of quinazolinone-2-thio-metronidazole derivatives 9a-o was designed, synthesized and assayed for their activities against metabolic enzymes human carbonic anhydrase I and II (hCAs I and II), acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and α-glucosidase. The results indicated that all the synthesized compounds exhibited excellent inhibitory activities against mentioned enzymes as compared with standard inhibitors. Representatively, the most potent compound against CA enzymes, 4-fluorophenyl derivative 9i, was 4 and 7-times more potent than standard inhibitor acetazolamide against hCA I and II, respectively; 4-fluorobenzyl derivative 9m as the most potent compound against cholinesterase enzymes, was around 11 and 21-times more potent than standard inhibitor tacrine against AChE and BChE, respectively; the most active α-glucosidase inhibitor 9h with 4-methoxyphenyl moiety was 5-times more active that acarbose as standard inhibitor. Furthermore, in order to study interaction modes of the most potent compounds in the active site of their related enzymes, molecular modeling was performed. Druglikeness, ADME, and toxicity profile of the compounds 9i, 9m, and 9h were also predicted.
- Ansari, Samira,Asgari, Mohammad Sadegh,Biglar, Mahmood,Esfahani, Ensieh Nasli,Hamedifar, Haleh,Larijani, Bagher,Mahdavi, Mohammad,Mohammadi-Khanaposhtani, Maryam,Rastegar, Hossein,Tas, Recep,Taslimi, Parham
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-
- Synthesis of 2-aryl quinazolinones: Via iron-catalyzed cross-dehydrogenative coupling (CDC) between N-H and C-H bonds
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Herein, we describe the direct synthesis of quinazolinones via cross-dehydrogenative coupling between methyl arenes and anthranilamides. The C-H functionalization of the benzylic sp3 carbon is achieved by di-t-butyl peroxide under air, and the subsequent amination-aerobic oxidation process completes the annulation process. Iron catalyzed the whole reaction process and various kinds of functional groups were tolerated under the reaction conditions, providing 31 examples of 2-aryl quinazolinones using methyl arene derivatives in yields of 57-95percent. The synthetic potential has been demonstrated by the additional synthesis of aryl-containing heterocycles. This journal is
- Jang, Yoonkyung,Lee, Seok Beom,Hong, Junhwa,Chun, Simin,Lee, Jeeyeon,Hong, Suckchang
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supporting information
p. 5435 - 5441
(2020/08/03)
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- A novel approach for the synthesis of functionalized hydroxylamino derivative of dihydroquinazolinones
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A new metal-free and modular approach for the synthesis of various functionalized dihydroquinazolinones has been developed from isatoic anhydride, amines, 4-chloro-N-hydroxybenzimidoylchloride to yield up to 71%. The reaction has been screened in various bases, solvents at different temperatures. The substrate scope of the reaction has been studied with various amines and the possible reaction mechanism for this reaction has also been proposed.
- Jaganmohan, Chikkanti,Vinay Kumar,Venkateshwarlu,Mohanty, Sandeep,Kumar, Jaydeep,Venkateswara Rao,Raghunadh, Akula,Tadiparthi, Krishnaji
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supporting information
p. 2163 - 2170
(2020/06/10)
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- Novel quinazolin–sulfonamid derivatives: synthesis, characterization, biological evaluation, and molecular docking studies
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In the design of novel drugs, the formation of hybrid molecules via the combination of several pharmacophores can give rise to compounds with interesting biochemical profiles. A series of novel quinazolin–sulfonamid derivatives (9a–m) were synthesized, characterized and evaluated for their in vitro antidiabetic, anticholinergics, and antiepileptic activity. These synthesized novel quinazolin–sulfonamid derivatives (9a–m) were found to be effective inhibitor molecules for the α-glycosidase, human carbonic anhydrase I and II (hCA I and hCA II), butyrylcholinesterase (BChE) and acetylcholinesterase (AChE) enzyme, with Ki values in the range of 100.62 ± 13.68–327.94 ± 58.21 nM for α-glycosidase, 1.03 ± 0.11–14.87 ± 2.63 nM for hCA I, 1.83 ± 0.24–15.86 ± 2.57 nM for hCA II, 30.12 ± 3.81–102.16 ± 13.87 nM for BChE, and 26.16 ± 3.63–88.52 ± 20.11 nM for AChE, respectively. In the last step, molecular docking calculations were made to compare biological activities of molecules against enzymes which are achethylcholinesterase, butyrylcholinesterase and α-glycosidase. Communicated by Ramaswamy H. Sarma.
- Sepehri, Nima,Mohammadi-Khanaposhtani, Maryam,Asemanipoor, Nafise,Hosseini, Samanesadat,Biglar, Mahmood,Larijani, Bagher,Mahdavi, Mohammad,Hamedifar, Haleh,Taslimi, Parham,Sadeghian, Nastaran,Norizadehtazehkand, Mostafa,Gulcin, Ilhami
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- Synthesis and biological evaluation of quinoline-quinazolinones for antimicrobial and antileishmanial potential
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In an attempt to find a new class of antimicrobial and antileishmanial agents, a series of twenty-three quinoline-quinazolinones were prepared via reaction of 8-hydroxy/methoxyquinoline-2-carbaldehyde with various substituted aminobenzamides. These compounds were screened for their antimicrobial activity against Gram-positive bacteria (B. subtilis), Gram-negative bacteria (E. coli and P. putida) and fungus (C. viswanathii) and antileishmanial activity against promastigotes of L. donovani. Compound 28k exhibited highest activity against B. subtilis with an IC50 of 0.17±0.07 M while compound 28j exhibited highest activity against promastigotes of L. donovani with an IC50 of 6±0.0 M.
- Tiwari, Shweta,Kirar, Seema,Banerjee, Uttam Chand,Babu, Neerupudi Kishore,Singh, Sushma,Singh, Inder Pal
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p. 1251 - 1258
(2020/12/04)
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- Sustainable methine sources for the synthesis of heterocycles under metal- and peroxide-free conditions
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Alcohols and ethers were identified as sustainable methine sources for synthesizing quinazolinone and benzimidazole derivatives using a combination of TsOH·H2O/O2 and appropriate bis-nucleophiles for the first time. Deuterium labeling studies clearly proved that the C2 hydrogen of the synthesized heterocycles came from the methine source. These unique reaction conditions were successfully applied to the synthesis of echinozolinone (2e′), 2f′ (a common precursor of rutaecarpine and (±) evodiamine), and dimedazole (6d). Notable features of this method include its low toxicity, use of commercial feedstocks as substrates, low cost, broad functional group tolerance and suitability for a wide range of bis-nucleophilic starting materials.
- Senadi, Gopal Chandru,Kudale, Vishal Suresh,Wang, Jeh-Jeng
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supporting information
p. 979 - 985
(2019/03/12)
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- Synthesis and anion recognition studies of new oligomethylene bis(nitrophenylureylbenzamide) receptors
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A new series of oligomethylene bis(nitrophenylureylbenzamide) receptors were synthesized varying the relative position of the urea and amide groups (ortho4 and meta8) and the length of the oligomethylene chain (C2 to C8). An anion re
- García-Elías, José,Ochoa-Terán, Adrián,Yatsimirsky, Anatoli K.,Santacruz Ortega, Hisila,Ochoa-Lara, Karen,López-Martínez, Luis Miguel,Castro-Riquelme, Christian L.,García, ángel L.,Madrigal-Peralta, Domingo,Labastida-Galván, Victoria,Ordo?ez, Mario
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p. 39147 - 39162
(2019/12/15)
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- Copper-Catalyzed Intramolecular α-C-H Amination via Ring-Opening Cyclization Strategy to Quinazolin-4-ones: Development and Application in Rutaecarpine Synthesis
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A copper-catalyzed intramolecular α-C-H amination has been developed for the synthesis of quinazolin-4(3 H)-one derivatives from commercially available isatoic anhydride and primary and secondary benzylamines via ring-opening cyclization (ROC). This method shows good functional group tolerance and allows access to a range of 2-aryl, 2-alkyl, and spiroquinazolinone derivatives. However, 2-methylquinazolin-4(3 H)-one was synthesized from 2-amino- N -isopropylbenzamide by C-C bond cleavage, and N -benzyl-2-(methylamino)benzamide afforded 1-methyl-2-phenylquinazolin-4(1 H)-one along with 2-phenylquinazolin-4(3 H)-one by N-C bond cleavage for aromatization. It is the first general method to construct the potentially useful 2-methylquinazolin-4(3 H)-one by copper-catalyzed intramolecular C-H amination. Also this ROC strategy has been successfully applied to the synthesis of quinazolinone alkaloid rutaecarpine.
- Biswal, Sonali,Chada, Harika,Patel, Srilaxmi M.,Sharada, Duddu S.,Sharma, Sonika
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p. 3160 - 3170
(2019/08/07)
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- Novel naphthalimide–aminobenzamide dyads as OFF/ON fluorescent supramolecular receptors in metal ion binding
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A series of novel naphthalimide–aminobenzamide (NAPIM-2ABZ) dyads 3 connected by different length polymethylene chains were synthesized and studied as fluorescent supramolecular receptors in metal ion binding. The photophysical properties were evaluated a
- Landey-álvarez, Marco A.,Ochoa-Terán, Adrián,Pina-Luis, Georgina,Martínez-Quiroz, Marisela,Aguilar-Martínez, Milagros,Elías-García, José,Miranda-Soto, Valentín,Ramírez, José-Zeferino,Machi-Lara, Lorena,Labastida-Galván, Victoria,Ordo?ez, Mario
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p. 892 - 906
(2016/10/24)
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- An efficient four-step approach toward fused triazino[1,6-a] quinazolines
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Herein, we describe a simple, four-step process for the preparation of 1,2,3-triazino[1,6-a]quinazolin-13-ones. This method involves ring-opening, quinazoline-forming condensation, reduction, diazotization accompanied by rapid intramolecular cyclization in the last step afforded the desired products with structurally complex heterocyclic core in excellent to high yields.
- Sayahi, Mohammad Hosein,Baghersaei, Shirin,Goli, Fereshteh,Moghimi, Setareh,Mahdavi, Mohammad,Firoozpour, Loghman,Shafiee, Abbas,Foroumadi, Alireza
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p. 189 - 192
(2016/05/09)
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- Novel β-carboline-quinazolinone hybrid as an inhibitor of Leishmania donovani trypanothione reductase: Synthesis, molecular docking and bioevaluation
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Trypanothione reductase (TR) is a vital enzyme in the trypanothione based redox metabolism of trypanosomatid parasites. It is one of the few chemically validated targets for Leishmania. Herein, we report the synthesis of novel β-carboline-quinazolinone hybrids that are able to inhibit Leishmania donovani TR (LdTR) and subsequently inhibit cell growth. A molecular modeling approach based on docking studies and subsequent binding free energy estimation was performed in the active site of LdTR to understand their possible binding sites. With the enzymatic assay on LdTR with compounds, we were able to identify six hit compounds (8j-8o) that were all found to be the competitive inhibitors of TR with Ki in the range of 0.8-9.2 μM. The whole-cell screening assay highlighted the analogues 8k, 8l and 8n as the most active compounds with IC50 of 4.4, 6.0 and 4.3 μM, respectively, along with an adequate selectivity index (SI) of >91, 36 and 24, respectively. This journal is
- Chauhan, Shikha S.,Pandey, Shashi,Shivahare, Rahul,Ramalingam, Karthik,Krishna, Shagun,Vishwakarma, Preeti,Siddiqi,Gupta, Suman,Goyal, Neena,Chauhan, Prem M. S.
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p. 351 - 356
(2015/03/18)
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- Synthesis and anticancer activity of N -substituted 2-arylquinazolinones bearing trans -stilbene scaffold
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A novel series of 2-arylquinazolinones 7a-o bearing trans-stilbene moiety were designed, synthesized, and evaluated against human breast cancer cell lines including human breast adenocarcinoma (MCF-7 and MDA-MB-231) and human ductal breast epithelial tumor (T-47D). Among the tested compounds, the sec-butyl derivative 7h showed the best profile of activity (IC50 5 μM) against all cell lines, being 2-fold more potent than standard drug, etoposide. Our investigation revealed that the cytotoxic activity was significantly affected by N3-alkyl substituents. Furthermore, the morphological analysis by acridine orange/ethidium bromide double staining test and flow cytometry analysis indicated that the prototype compound 7h can induce apoptosis in MCF-7 and MDA-MB-231 cells.
- Mahdavi, Mohammad,Pedrood, Keyvan,Safavi, Maliheh,Saeedi, Mina,Pordeli, Mahboobeh,Ardestani, Sussan Kabudanian,Emami, Saeed,Adib, Mehdi,Foroumadi, Alireza,Shafiee, Abbas
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p. 492 - 499
(2015/04/14)
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- Solvent-free synthesis of novel benzodiazepine derivatives by a three-component base-catalysed reaction of isatoic anhydride, a primary amine and chloroacetyl chloride
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Heating isatoic anhydride with a series of primary amines at 150 °C under solvent-free conditions yielded 2-amino-N-alkylbenzamides which, in the same pot, reacted readily with chloroacetyl chloride in the presence of poly(dimethylaminoethyl acrylamide)-modified magnetic nanoparticles (MNP@PDMA), a base catalyst, to give 4-alkyl-1,4-benzodiazepine-2,5-diones in good yields without formation of by-products.
- Seydey, Mohsen Khalilpour,Rezaei, Zahra,Homami, Seyed Saied
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p. 286 - 288
(2015/06/02)
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- A highly efficient method for the synthesis of novel 1'H-spiro[indene-2,2'-quinazoline]-1,3,4'(3'H)-trione derivatives
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A series of novel ninhydrin-derived spiro-quinazolinone derivatives in moderate to good yields have been synthesised through a ferric chloride catalysed reaction in 1,2-dichloroethane.
- Sadat-Ebrahimi, Seyed Esmail,Irannezhad, Soroor,Moghimi, Setareh,Yahya-Meymandi, Azadeh,Mahdavi, Mohammad,Shafiee, Abbas,Foroumadi, Alireza
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p. 495 - 498
(2015/11/27)
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- Metal-free oxidative synthesis of quinazolinones via dual amination of sp3 C-H bonds
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A novel metal-free synthesis of quinazolinones via dual amination of sp3 C-H bonds was developed. The sp3 carbon in methylarenes or adjacent to a heteroatom in DMSO, DMF or DMA was used as the one carbon synthon. This journal is the Partner Organisations 2014.
- Zhao, Dan,Wang, Teng,Li, Jian-Xin
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supporting information
p. 6471 - 6474
(2014/06/09)
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- Convenient and sequential one-pot route for synthesis of 2-thioxoquinazolinone and quinazolinobenzothiazinedione derivatives
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A new and efficient synthetic process has been developed for preparation of 2-thioxoquinazolinone and quinazolinobenzothiazinedione derivatives. The related products were synthesized through reaction of isatoic anhydride, amines/anthranilic acids, and carbon disulfide (CS2) in the presence of potassium hydroxide in ethanol at reflux. Graphical abstract: [Figure not available: see fulltext.]
- Asadi, Mehdi,Masoomi, Shiva,Ebrahimi, Seyed Mostafa,Mahdavi, Mohammad,Saeedi, Mina,Shafiee, Abbas,Foroumadi, Alireza
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p. 497 - 504
(2014/03/21)
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- Novel four-step synthesis of thioxo-quinazolino[3,4- A ]quinazolinone derivatives
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A novel synthesis of thioxo-quinazolino[3,4-a]quinazolinone framework was developed through a four-step reaction starting from isatoic anhydride. The resulting 2-aminobenzamides from the reaction of isatoic anhydride and different amines underwent coupling-cyclization reaction with 2-nitrobenzaldehydes, reduction of nitro group, and then cyclization reaction with carbon disulfide (CS2). All steps were carried out under easy and user-friendly conditions in a short time without using expensive catalysts or reagents. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]
- Shafii, Behnaz,Saeedi, Mina,Mahdavi, Mohammad,Foroumadi, Alireza,Shafiee, Abbas
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supporting information
p. 215 - 221
(2013/12/04)
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- Structural optimization of a retrograde trafficking inhibitor that protects cells from infections by human polyoma- and papillomaviruses
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Human polyoma- and papillomaviruses are non-enveloped DNA viruses that cause severe pathologies and mortalities. Under circumstances of immunosuppression, JC polyomavirus causes a fatal demyelinating disease called progressive multifocal leukoencephalopathy (PML) and the BK polyomavirus is the etiological agent of polyomavirus-induced nephropathy and hemorrhagic cystitis. Human papillomavirus type 16, another non-enveloped DNA virus, is associated with the development of cancers in tissues like the uterine cervix and oropharynx. Currently, there are no approved drugs or vaccines to treat or prevent polyomavirus infections. We recently discovered that the small molecule Retro-2cycl, an inhibitor of host retrograde trafficking, blocked infection by several human and monkey polyomaviruses. Here, we report diversity-oriented syntheses of Retro-2cycl and evaluation of the resulting analogs using an assay of human cell infections by JC polyomavirus. We defined structure-activity relationships and also discovered analogs with significantly improved potency as suppressors of human polyoma- and papillomavirus infection in vitro. Our findings represent an advance in the development of drug candidates that can broadly protect humans from non-enveloped DNA viruses and toxins that exploit retrograde trafficking as a means for cell entry.
- Carney, Daniel W.,Nelson, Christian D.S.,Ferris, Bennett D.,Stevens, Julia P.,Lipovsky, Alex,Kazakov, Teymur,Dimaio, Daniel,Atwood, Walter J.,Sello, Jason K.
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p. 4836 - 4847
(2014/10/16)
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- Synthesis, antimicrobial evaluation, ot-QSAR and mt-QSAR studies of 2-amino benzoic acid derivatives
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A series of 2-amino benzoic acid derivatives (1-28) were synthesized and evaluated for their in vitro antimicrobial activity against the panel of Gram positive, Gram negative bacterial and fungal strains. The results of antimicrobial studies indicated that, in general, the synthesized compounds were found to be bacteriostatic and fungistatic in action. QSAR studies performed by the development of one target and multi target models indicated that multi-target model was effective in describing the antimicrobial activity as well demonstrated the effect of structural parameters viz. LUMO, 3χv and W on antimicrobial activity of 2-amino benzoic acid derivatives. Springer Science+Business Media, LLC 2010.
- Mahiwal, Kuldeep,Kumar, Pradeep,Narasimhan, Balasubramanian
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experimental part
p. 293 - 307
(2012/09/07)
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- Fused bicyclic derivatives of 2,4-diaminopyrimidine as c-Met inhibitors
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The HGF-c-Met signaling axis is an important paracrine mediator of epithelial-mesenchymal cell interactions involving the regulation of multiple cellular activities including cell motility, mitogenesis, morphogenesis, and angiogenesis. Dysregulation of c-Met signaling (e.g., overexpression or increased activation) is associated with the development of a wide range of tumor types; thus, inhibiting the HGF-c-Met pathway is predicted to lead to anti-tumor effects in many cancers. Elaboration of a 2-arylaminopyrimidine scaffold led to a series of potent c-Met inhibitors bearing a C4-2-amino-N-methylbenzamide group. Specifically, a series of C2-benzazepinone analogs demonstrated potent inhibition of c-Met in enzymatic and cellular assays. Kinase selectivity could be tuned by varying the nature of the alkyl group on the benzazepinone nitrogen.
- Weinberg, Linda R.,Albom, Mark S.,Angeles, Thelma S.,Husten, Jean,Lisko, Joseph G.,McHugh, Robert J.,Milkiewicz, Karen L.,Murthy, Seetha,Ott, Gregory R.,Theroff, Jay P.,Tripathy, Rabindranath,Underiner, Ted L.,Zificsak, Craig A.,Dorsey, Bruce D.
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p. 164 - 167
(2011/03/17)
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- Nucleotides. Part LXXVIII: Double labeling of nucleosides and nucleotides
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Several N(-hydroxyalkyl)-2,4-dinitroanilines were transformed into their phosphoramidites (see 5 and 6 in Scheme 1) in view of their use as fluorescence quenchers, and modified 2-aminobenzamides (see 9, 10, 18, and 19 in Scheme 1) were applied in model re
- Maier, Thomas,Pfleiderer, Wolfgang
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experimental part
p. 2365 - 2392
(2011/02/18)
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- A regioselective three-component reaction for synthesis of novel 1′H-spiro[isoindoline-1,2′-quinazoline]-3,4′(3′H)-dione derivatives
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A ring opening and regioselective three-component reaction of isatoic anhydride, isatins, and aromatic or aliphatic primary amines in the presence of catalytic amount of KAl(SO4)2·12H2O (alum) to yield a novel series of 1′H-spiro[isoindoline-1,2′-quinazoline]-3,4′(3′H)-dione is described.
- Mohammadi, Ali A.,Dabiri,Qaraat
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body text
p. 3804 - 3808
(2009/09/05)
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- Development of novel 2-[4-(aminoalkoxy)phenyl]-4(3H)-quinazolinone derivatives as potent and selective histamine H3 receptor inverse agonists
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Novel 2-[4-(aminoalkoxy)phenyl]-4(3H)-quinazolinone derivatives were identified as potent human H3 receptor inverse agonists. After systematic modification of lead 5a, the potent and selective analog 5r was identified. Elimination of hERG K+ channel and human α1A-adrenoceptor activities is the main focus of the present study.
- Mizutani, Takashi,Nagase, Tsuyoshi,Ito, Sayaka,Miyamoto, Yasuhisa,Tanaka, Takeshi,Takenaga, Norihiro,Tokita, Shigeru,Sato, Nagaaki
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scheme or table
p. 6041 - 6045
(2009/06/30)
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- Imidazoline derivatives as alpha-1A adrenoceptor ligands
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Compound of formula (I) or a pharmaceutically acceptable salt or solvate thereof are disclosed. Such compounds are useful in the treatment of Alpha-1A mediated diseases or conditions such as urinary incontinence.
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Page/Page column 17
(2010/02/11)
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- An unusual addition and ring-closure reaction of 1-(2-bromoethyl)-2,3-dihydro-3-propyl-1,3,2-benzo-diazaphosphorin-4(1H)-one 2-oxide with carbon disulfide for a new and convenient synthesis of the fused phosphorus heterocyclic compound
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The reaction of 1-(2-bromoethyl)-2,3-dihydro-3-propyl-1,3,2- benzodiazaphosphorin-4(1H)-one 2-oxide with carbon disulfide takes an alternative pathway in the use of different bases. The sodium hydride mediated reaction leads to the formation of the tricyclic fused 1,2,3,4,4a,4b,5,6-octahydro-6-oxo-5-propyl-4-thia-3,4b,4a -thiazphosphaphenanthridine 4a-oxide via addition of H-P bond across the double bond of carbon disulfide followed by intramolecular cyclization. In the presence of triethylamine, refluxing a mixture of 1-(2-bromoethyl)-2,3-dihydro-3-propyl-1,3,2-benzodiazaphosphorin-4(1H)-one 2-oxide with carbon disulfide in benzene takes an unusual course with formation in excellent yield of the first example of fused phosphorus heterocyclic 4-[1′-(β-bromoethyl)-4′-oxo-3′-propyl-1′, 2′,3′,4′-tetrahydro-1,3,2-benzodiazaphosphorin-2′ -sulfide]-1,2,3,4,4a,4b,5,6-octahydro-6-oxo-5-propyl-3,4b, 4a- thiazphosphaphenanthridine 4a,2′-dioxide, which was confirmed by spectroscopic methods, microanalyses and single crystal X-ray structure determination.
- Huang, Jun-Min,Chen, Hui,Chen, Ru-Yu
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p. 2215 - 2225
(2007/10/03)
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- Efficient synthesis and crystal structure of 2-propyl-5-(substituted)phenyl-1,4-dioxo-1,2,3,4,5,6,7,8-octahydro-[1,4,2]diazap hosphorino[1,2-a][1,3,2]benzodiazaphosphorine 3-oxides
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In order to search for novel antitumor and antiviral agents with high activity and low toxicity, some 2-propyl-5-(substituted)phenyl-1,4-dioxo-1,2,3,4,5,6,7,8-octahydro-[1,4,2]diazap hosphorino[1,2-a][1,3,2]benzodiazaphosphorine 3-oxides (2a-e) have been designed incorporating the proximate carbonyl and phosphoryl groups into the benzoannulated phosphadiamide heterocycle and synthesized in acceptable yields. These compounds contain the proximate carbonyl and phosphoryl groups in the fused heterocycle. Their structures were confirmed by spectroscopic methods and microanalyses. The results from X-ray crystallography analysis of 2a showed that the proximate carbonyl and phosphoryl groups are not coplanar because of their being jointly located in the fused heterocycle, having ring tension, and this then destroys the conjugation between the C=O and the P=O moieties. As a result, the length of the P-C bonds measured as 1.851(3)-1.852(3) A are just the same as that of a P-C bond not involved in conjugation (1.80-1.85 A). Also, the C(1), C(2), C(3), N(2), N(3), and P(1) atoms of the [1,4,2]diazaphosphorino moiety exist preferably in the boat conformation. The coplanar C(1), C(3), N(2), and N(3) atoms, within an average deviation of 0.0102, A, form the ground floor of the boat conformation, whereas the P(1) and C(2) atoms are on the same side of the coplanar structure with the distance of 0.7067 and 0.6315 A, respectively.
- Huang, Junmin,Chen, Hui,Chen, Ruyu
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- Synthesis and crystal structure of 2-propyl-5-phenyl-1, 4-dioxo-1,2,3,4,5,6,7,8-octahydro-[1,4,2]diazaphosphorino [1,2-a][1,3,2]benzodiazaphosphorine 3-oxide
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The synthesis and structure characterization of 2-propyl-5-phenyl-1,4-dioxo-1,2,3,4,5, 6,7,8-octahydro-[1,4,2]diazaphosphorino[1,2-a][1,3,2]benzodiazaphosphorine 3-oxide are described. The title compound has been designed to incorporate proximate carbonyl and phosphoryl groups in a heterocycle fused to benzophosphadiamide heterocycle. Crystal data: C19H20N3O3P, Monoclinic, space group P2(1)/c, with a = 9.7585(9) A, b = 21.4319(19) A, c= 17.7900(16) A, β = 100.823(2)°, Z = 8, V = 3654.5(6) A3. The crystal structure shows that the proximate carbonyl and phosphoryl groups are not coplanar, and the [1,4,2]diazaphosphorino moiety prefers the boat conformation.
- Huang, Junmin,Chen, Hui,Chen, Ruyu
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p. 445 - 452
(2007/10/03)
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- Benzoylaminoquinazolinones
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This invention is compounds of the formula: STR1 and a method of treating cognitive and related neuronal behavioral problems in mammals using the compounds.
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