Synthesis, physicochemical and biological evaluation of 2-amino-5-chlorobenzophenone derivatives as potent skeletal muscle relaxants

 

Rajesh Singh

M. Pharm., PhD, AIC

Professor (Assistant)

Punjab Technical University, Jalandhar · Faculty of Pharmacy 

 

• 
  Punjab Technical University

  Faculty of Pharmacy

  Jalandhar, India

 

 link

 https://plus.google.com/115046907236504581005/about

 rksingh244@gmail.com

About

Dr Singh, educational qualifications from Panjab Univ., Chandigarh, GATE (2003) with 92.26 percentile, elected member of Association of Institution of Chemist (AIC), above 9 years of teaching experience and guided 16 PG students. He has to his credit > than 35 scientific research papers in reputed referred indexed journals, 40 res. presen., 1 book, 6 best paper presentation awards and 5 res. projects funded by PSCST, Chd. He is registered Pharmacist of Punjab State and life member of APTI.

Figure 1.

Important pharmacophore of 1,4-benzodiazepine nucleus.

Scheme 1.

Synthesis of 2-amino-5-chloro-benzophenone derivatives (3a–3g)

2.3.3. 2-(4′-Chloroanilino)acetamido-5-chlorobenzophenone (3a)

IR (KBr cm⁻¹): 3346 (Sec N–H str), 3100 (Aromatic C–H str), 2984 (Aliphatic C–H str), 1661 (CO str), 1487 (Aromatic CC str), 1229 (C–N str) and 761 (C–Cl str) ¹H NMR (DMSO-d₆ 1δ ppm): 4.19 (s, 2H, –COCH₂N), 7.26–8.60 (m, 12H, Ar–H) and 11.46 (br s, 1H, –NHCOCH₂–) Anal. Calcd. for C₂₁H₁₆ N₂O₂Cl_2: C, 63.17; H, 4.04; N, 7.02; Found: C, 63.07; H, 4.02; N, 7.09.

 1H NMR PREDICT

Arabian Journal of Chemistry

Volume 8, Issue 3, May 2015, Pages 307–312

Original article

Synthesis, physicochemical and biological evaluation of 2-amino-5-chlorobenzophenone derivatives as potent skeletal muscle relaxants

• Rajesh K. Singh^, ,
• Sonia Devi¹,
• D.N. Prasad

• Pharmaceutical Chemistry Division, Shivalik College of Pharmacy, Nangal, Rupnagar, Punjab 140126, India

Received 7 June 2011, Accepted 22 November 2011, Available online 3 December 2011

Open Access funded by King Saud University

Under a Creative Commons license

http://www.sciencedirect.com/science/article/pii/S187853521100298X

doi:10.1016/j.arabjc.2011.11.013

Corresponding author. Tel.: +91 01887 221276, mobile: +91 9417513730; fax: +91 01887 221276   rksingh244@gmail.com

1 Present Address: Dept. of Pharmaceutical Chemistry, Laureate Institute of Pharmacy, Kathog, Kangra, Himachal Pradesh, India.


Take a tour

 Pharmaceutical Chemistry Division, Shivalik College of Pharmacy, Nangal, Rupnagar, Punjab 140126, India












Dept. of Pharmaceutical Chemistry, Laureate Institute of Pharmacy, Kathog, Kangra, Himachal Pradesh, India.

 






Bhakra Dam, about 12 km from Nangal, the tallest dam of Asia


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Nucleophilic Aromatic Substitution of 5-fluoro-1-indanone with morpholine ......5-morpholino-1-indanone

5-Morpholino-1-indanone

.

Nucleophilic Aromatic Substitution of 5-fluoro-1-indanone with morpholine

 The synthesis was performed using standard Schlenk techniques under a nitrogen atmosphere.  To a dried and nitrogen flushed glass microwave reaction vial was added  5-flouro-1-indanone (0.101 g, 0.67 mmol).  The vial's atmosphere was cycled four times. Morpholine (2.0 mL, 0.023 mol, 3.47 equivs.) was added, The reaction was then sealed and heated to 100 ^oC for 20 hours under variable watt microwave heating.  At the completion of the reaction the crude material was transferred to a 50 mL round bottom flask using 3.5 mL ethyl acetate. Silica and ethyl acetate (4.5 mL) were added to the flask and the solvent was removed under reduced pressure to yield a free flowing dry load.  The crude product was then subjected to purification via flash chromatography (75 : 25 ethyl acetate : hexanes) to yield a red solid (144 mg, 98.7%).

¹H NMR:  (CDCl₃) δ ppm 2.59-2.62 (m, 2H), 3.01 (t, J=5.7 Hz, 2H), 3.30 (t, J=5.0 Hz, 4H), 3.83 (t, J=4.7 Hz, 4H), 6.78 (m, 6.78-6.79, 1H), 6.83-6.86 (m, 1H), 7.61 (d, J=8.8 Hz, 1H).

¹³C NMR:  (CDCl₃) δ ppm 25.8, 36.3, 47.6, 66.4, 109.7, 114.0, 124.9, 128.2, 155.8, 157.7, 204.9

GCMS EI [M⁺]  Predicted: 217.2, Actual: 217


see


5-morpholino-1-indanone-1H.pdf
5-morpholino-1-indanone-13C.pdf
GCMS Data 5-morpholino-1-indanone.pdf

GCMS EI [M+]  Predicted: 217.2, Actual: 217

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HELP TO INTERPRET USING RELATED 

MOLECULES.....U CAN LEARN

SOME OTHER INDANONES

Chern, C.-Y.; Yek, Y.-L.; Chen, Y.-L.; Kan, W.-M. J. Chin. Chem. Soc. 2008, 55, 846–853.

Dinges, J.; Albert, D.H.; Arnold, L.D.; Ashworth, K.L.; et al J. Med Chem. 2007, 50, 2011-2029

 

The resonance assignment of 2-ethyl-1-indanone 

References

Chern, C.-Y.; Yek, Y.-L.; Chen, Y.-L.; Kan, W.-M. J. Chin. Chem. Soc. 2008, 55, 846–853.

Dinges, J.; Albert, D.H.; Arnold, L.D.; Ashworth, K.L.; et al J. Med Chem. 2007, 50, 2011-2029

 


The first enantioselective synthesis of (−)-conolutinine was achieved in 10 steps. The synthesis featured a catalytic asymmetric bromocyclization of tryptamine to forge the tricycle intermediate. Hydration of an alkene catalyzed by Co(acac)₂ was also employed as a key step to diastereoselectively introduce the tertiary alcohol moiety. The absolute configuration of (−)-conolutinine was established to be (2S,5aS,8aS,13aR) based on this asymmetric total synthesis.

 

 

Total Synthesis of (−)-Conolutinine

Xiangyang Feng^†‡, Guangde Jiang^‡, Zilei Xia^‡, Jiadong Hu^†‡, Xiaolong Wan^§, Jin-Ming Gao^†, Yisheng Lai^*‡, and Weiqing Xie^*†§

^† Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Science, Northwest A&F University, 22 Xinong Road, Yangling 712100, Shaanxi, China

^‡ State Key Laboratory of Natural Medicines, Jiangsu Key Laboratory of Drug Discovery for Metabolic Diseases, Center of Drug Discovery, China Pharmaceutical University, 24 Tongjiaxiang, Nanjing 210009, China

^§ State Key Laboratory of Bioorganic & Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China

Org. Lett., Article ASAP

DOI: 10.1021/acs.orglett.5b02046

http://pubs.acs.org/doi/abs/10.1021/acs.orglett.5b02046

 http://pubs.acs.org/doi/suppl/10.1021/acs.orglett.5b02046/suppl_file/ol5b02046_si_001.pdf

*E-mail: yslai@cpu.edu.cn., *E-mail: xiewq@nwafu.edu.cn.

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Multistep Flow Synthesis of 5-Amino-2-aryl-2H-[1,2,3]-triazole-4- carbonitriles

Using the Uniqsis FlowSyn flow chemistry system researchers from the UCB Biopharma. Belgium have developed a flow synthesis of 2-substituted 1,2,3-triazoles that demonstrates improvements over the conventional batch route.

The route involves the diazotisation of anilines and condensation with malononitrile followed by the nucleophilic addition of ammonia or an alkylamine and finally a novel copper catalysed cyclisation. The intermediate azide was generated and consumed in situ which enabled safe scale up under the flow-through conditions employed.

 

J. Jacq, P. Pasau, Chem Eur. J., 2014, 20, (38), 12223.