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Friday 10 October 2014

Nabriva’s lefamulin, BC 3781

Nabriva’s lefamulin, BC 3781

2D chemical structure of 1061872-97-6
Nabriva’s lefamulin receives FDA fast-track status to treat CABP and ABSSS
Austria-based Nabriva Therapeutics has received qualified infectious disease product (QIDP) and fast-track status designation from the US Food and Drug Administration for its lefamulin (BC 3781).
read
Antibiotics 02 00500 i025
BC-3781
Topical pleuromutilin antibiotic agent
Gram-positive, including MRSA, PHASE 2 COMPLETED,Infection, acute bacterial skin and skin structure (ABSSSI)
Nabriva (Austria), Nabriva Therapeutics AG
BC-3781
cas 1061872-97-6
UNII-61H04Z5F9K
(3aS,4R,5S,6S,8R,9R,9aR,10R)-5-Hydroxy-4,6,9,10-tetramethyl-1-oxo-6-vinyldecahydro-3a,9-propanocyclopenta[8]annulen-8-yl [[(1R,2R,4R)-4-amino-2-hydroxycyclohexyl]sulfanyl]acetate;
14-O-[2-[(1R,2R,4R)-4-Amino-2-hydroxycyclohexylsulfanyl]acetyl]mutilin

lH NMR (400 MHz, CDC13, ppm, inter alia) δ 6.51 – 6.44 (m, 1H), 5.78 (d, J=8Hz, 1H), 5.38 – 5.20 (m, 2H), 3.48 – 3.40 (m, 1H), 3.36 (d, J=7Hz, 1H), 3.25 (AB, J=15Hz, 2H), 2.92 – 2.82 (m, 1H), 2.6 – 2.5 (m, 1H), 1.45 (s, 3H), 1.20 (s, 3H), 0.88 (d, J=7Hz, 3 H), 0.73 (d, J=8Hz, 3H)
MS (ESI, g/mol): m/z 508 [M+H] +

Tuesday 7 October 2014

Applications of Mass Spectrometry...on November 20, 2014 at CSIR-Indian Institute of Chemical Technology, Hyderabad, India


AMS14.jpg







Dr Sanjay Bajaj





Dr Sanjay Bajaj
Managing Director at Select Biosciences India

or see
http://selectbiosciences.com/conferences/index.aspx?conf=AMS14

SELECTBIO welcome you all at the International Conference on Applications of Mass Spectrometry scheduled to be held on November 20, 2014 at CSIR-Indian Institute of Chemical Technology, Hyderabad, India

Mass Spectrometry, has now become the most powerful analytical tool in almost every scientific discipline. This conference focuses on the instrumentation, tools, interpretation of results, applications, advances and new perspectives of Mass Spectrometry in the fields of Pharmaceuticals, Clinical, Genomics, Proteomics, Forensic, Environmental sciences etc. Attending this event will provide you with excellent opportunity for networking with like minded peers, helping you to build new relationships and optimize your workflow. 

This event is co-located with specialized event related to use of Mass Spectrometry in Pharmaceutical Analysis i.e.Advances in Forced Degradation Studies of Pharmaceuticals. Running alongside the conference will be an exhibition covering the latest technological advances and associated services within this field. 

Confirmed Speakers to date

Saranjit Singh, Professor/Head, National Institute of Pharmaceutical Education and Research
Jurgen H Gross, Head Mass Spectrometry Lab, Heidelberg University
R Srinivas, Head, NCMS, Indian Institute of Chemical Technology
Utpal Tatu, Professor, Indian Institute of Science
Mariappanadar Vairamani, Dean, SRM University

Call for Posters

You can also present your research on a poster while attending the meeting. Submit an abstract for consideration now!
Poster Submission Deadline: 31 October 2014

Agenda Topics

  • Applications in Genomics, Proteomics, Metabolomics & Lipidomics
  • In Lab Mass Spectrometry Workshop
  • Mass Spectrometry – Instrumentation and tools
  • Mass Spectrometry for Qualitative and Quantitative Analysis of Pharmaceuticals
  • Mass Spectrometry-Current Approaches and New Vistas

Sponsorship and Exhibition Opportunities

Maninderjit Singh, Exhibition Manager
mjsingh@selectbio.com
7696225050

Thursday 2 October 2014

2-PENTANONE



2-PENTANONE

1) In the NMR spectrum, we note that there are 4 distinct peaks, so we know that in the molecule, there are four different types of hydrogens.
2) The area of the individual peaks gives the sum of 10, in line with the empirical formula C 5 H 10 O, so the area declared at the top of the peaks corresponds to the number of hydrogen atoms that produce that signal.
3) The molecule C 5 H 10 O contains a double bond, in fact if it were saturated with hydrogens would contain 12 (2n + 2). Because it contains a carbonyl, the double bond is here, the rest of the molecule is saturated.
4) The two signals at d 2.45 and d 2.09 corresponding to the hydrogens on the carbon next to the carbonyl which absorb in the range between d 2 and d 3. The other two peaks at d 0.96 and d 1.61 corresponding to hydrogen instead of carbon primary and secondary respectively.
5) The peak 2 at d 2.09 has multiplicity 1 then refers to hydrogens that do not have near no hydrogen (m - 1 0 = H). This confirms the previous inference that the peak is due to a CH 3 near the bunker.

The peak 1 at d 2.45 has multiplicity 3 then refers to hydrogens which have close idogeni 2 (m - 1 = 2 H). This confirms the previous inference that the peak is attributable to a CH 2 near a bunker, and also suggests that there is a further CH 2 tied immediately over.

The peak 3 at d 1.61 has multiplicity 6 then refers to hydrogens that are near 5 hydrogens (m - 1 = 5 H). This confirms the previous inference that the peak is due to a CH 2 secondary that has near the two hydrogens of the peak 1 and the other three hydrogen atoms, those of the CH 3terminal.

The peak 4 at d 0.96 has multiplicity 3 then refers to hydrogens which have close idogeni 2 (m - 1 = 2 H). This confirms the previous inference that the peak is due to the CH 3 terminal of the molecule.

6)
 The deductions made ​​so far lead us to hypothesize that the NMR spectrum is related to the molecule 2-pentanone which has the structure shown at right:

7)
 Analyzing the molecule of 2-pentanone we can confirm the assignment of the peaks for both the chemical shift, both for the multiplicity (indicated in the figure in parentheses.)
 
2-pentanone




IR



MASS



13 CNMR




RAMAN

Saturday 27 September 2014

(S)-Atenolol

Figure US06982349-20060103-C00001
(S)-Atenolol
  • Selective β1 adrenoceptor antagonist
  • Biological descriptionSelective βadrenoceptor antagonist. Orally active. Limited ability to cross the blood-brain barrier. Antihypertensive activity in vivo.

Properties

  • Chemical name(S)-(-)-4-[2-Hydroxy-3-[(1-methylethyl)amino]propoxy]benzeneacetamide
  • Molecular Weight 266.34
  • Molecular formula C14H22N2O3
  • CAS Number 93379-54-5

m.p. 152–153° C.

[α]D 25: −17.2 (c=1.0, 1N HCl).

IR: νmax 3352, 3168, 1635, 1242 cm−1.

1H NMR (DMSO-d6): δ 0.99 (d, J=7 Hz, 6H, 2×CH3), 2.60 (m, 1H, CH), 2.74 (m, 2H, CH2), 3.27 (s, 2H, CH2), 3.88 (m, 4H, CH2, CH, NH), 6.83 (d, J=8 Hz, 2H, Ar—H), 7.14 (d, J=8 Hz, 2H, Ar—H), 7.40 (bs, 1H).


13C NMR (DMSO-d6):
22.01, 22.09,
41.26, 48.39, 49.38, 67.73, 70.58, 114.16, 128.41, 129.93, 157.17, 172.59 ppm.

Thursday 25 September 2014

COBICISTAT

Cobicistat, GS-9350
1004316-88-4
40 H 53 N 7 O 5 S 2
N-[1(R)-Benzyl-4(R)-[2(S)-[3-(2-isopropylthiazol-4-ylmethyl)-3-methyl]ureido]-4-(4-morpholinyl)butyramido]-5-phenylpentyl]carbamic acid thiazol-5-ylmethyl ester
(1,3-thiazol-5-yl) methyl (5S, 8R, 11R) -8,11-dibenzyl-2-methyl-5-[2 - (morpholin-4-yl) ethyl] -1 – [2 - (propan-2-yl) -1,3-thiazol-4-yl] -3,6-dioxo-2 ,4,7,12-tetraazatridecan-13-oate
cytochrome P450 3A4 (CYP3A4) inhibitor

Cobicistat (GS-9350): A potent and selective inhibitor of human CYP3A as a novel pharmacoenhancer
ACS Med Chem Lett 2010, 1(5): 209
Abstract Image



1-Benzyl-4-{2-[3-(2-isopropyl-thiazol-4-ylmethyl)-3-methyl-ureido]-4-morpholin-4-yl-butyrylamino}-5-phenyl-pentyl)-carbamic acid thiazol-5-ylmethyl ester (GS-9350)
HPLC (Chiral CelROD-H, Chiral Technologies Inc;heptane/iPrOH = 70/30).
1H NMR (CD3OD)
δ8.98 (1 H, s), 7.82 (1 H, s), 7.25-7.05
(11 H, m), 5.25-5.10 (2 H, m), 4.60-4.50 (2 H, m), 4.21-4.03 (2 H, m), 3.82-3.72 (1
H, m), 3.65-3.65 (4 H, m), 3.35-3.25 (1 H, m), 2.98 (3 H, s), 2.8-2.6 (4 H, m), 2.4-2.2
(6 H, m), 1.95-1.8 (1 H, m), 1.8-1.6 (1 H, m), 1.6-1.4 (4 H, m), 1.42-1.32 (6 H, m).
MS (ESI) m/z: 776.2 (M+H)+.
HRMS calc. for C40H53N7O5S2: 775.355, found: 775.353.



US 2014088304
The product I was isolated as the stock solution in ethanol (35.0 kg product, 76.1% yield).
1H NMR (dDMSO) δ□ 9.05 (s, 1H), 7.85 (s, 1H), 7.52 (d, 1H), 7.25-7.02 (m, 12H), 6.60 (d, 1H), 5.16 (s, 2H), 4.45 (s, 2H), 4.12-4.05 (m, 1H), 3.97-3.85 (m, 1H), 3.68-3.59 (m, 1H), 3.57-3.45 (m, 4H), 3.22 (septets, 1H), 2.88 (s, 3H), 2.70-2.55 (m, 4H), 2.35-2.10 (m, 6H), 1.75 (m, 1H), 1.62 (m, 1H), 1.50-1.30 (m, 4H), 1.32 (d, 6H).
13C NMR (CD3OD) δ 180.54, 174., 160.1, 157.7, 156.9, 153.8, 143.8, 140.1, 140.0, 136.0, 130.53, 130.49, 129.4, 127.4, 127.3, 115.5, 67.7, 58.8, 56.9, 55.9, 54.9, 53.9, 51.6, 49.8, 42.7, 42.0, 35.4, 34.5, 32.4, 32.1, 29.1, 23.7.


http://makeinindia.com/ MAKE IN INDIA
http://makeinindia.com/
http://makeinindia.com/sector/pharmaceuticals/

Wednesday 24 September 2014

Synthesis, biological evaluation and docking analysis of 3-methyl-1-phenylchromeno[4,3-c]pyrazol-4(1H)-ones as potential cyclooxygenase-2 (COX-2) inhibitors


STR4
COMPD HAS  cas no 1616882-93-9
MF……….C18 H11 F3 N2 O2
[1]​Benzopyrano[4,​3-​c]​pyrazol-​4(1H)​-​one, 3-​methyl-​1-​[4-​(trifluoromethyl)​phenyl]​-
 3-Methyl-1-(4-(trifluoromethyl)phenylchromeno[4,3-c]pyrazol-4(1H)-one
image

Synthesis, biological evaluation and docking analysis of 3-methyl-1-phenylchromeno[4,3-c]pyrazol-4(1H)-ones as potential cyclooxygenase-2 (COX-2) inhibitors

DOI: 10.1016/j.bmcl.2014.08.050
Jagdeep Grover, Vivek Kumar, M. Elizabeth Sobhia, Sanjay M. Jachak

 Abstract

As a part of our continued efforts to discover new COX inhibitors, a series of 3-methyl-1-phenylchromeno[4,3-c]pyrazol-4(1H)-ones were synthesized and evaluated for in vitro COX inhibitory potential. Within this series, seven compounds (3ad3h3k and 3q) were identified as potential and selective COX-2 inhibitors (COX-2 IC50’s in 1.79–4.35 μM range; COX-2 selectivity index (SI) = 6.8–16.7 range). Compound 3b emerged as most potent (COX-2 IC50 = 1.79 μM; COX-1 IC50 >30 μM) and selective COX-2 inhibitor (SI >16.7). Further, compound 3b displayed superior anti-inflammatory activity (59.86% inhibition of edema at 5 h) in comparison to celecoxib (51.44% inhibition of edema at 5 h) in carrageenan-induced rat paw edema assay. Structure–activity relationship studies suggested that N-phenyl ring substituted with p-CF3 substituent (3b3k and 3q) leads to more selective inhibition of COX-2. To corroborate obtained experimental biological data, molecular docking study was carried out which revealed that compound 3b showed stronger binding interaction with COX-2 as compared to COX-1.

Authors
  • a Department of Natural Products, National Institute of Pharmaceutical Education and Research, Sector-67, S.A.S. Nagar (Mohali) 160062, Punjab, India
  • b Department of Pharmacoinformatics, National Institute of Pharmaceutical Education and Research, Sector-67, S.A.S. Nagar 160062, Punjab, India
Sanjay Corresponding author. Tel.: +91 172 2214683; fax: +91 172 2214692.
 CLICK……….
Cyclooxygenase (COX) or prostaglandin endoperoxide synthase (PGHS), catalyzes the conversion of arachidonic acid to inflammatory mediators such as prostaglandins (PGs), prostacyclins and thromboxanes. COX exists in mainly two isoforms: COX-1 and COX-2.Nonsteroidal anti-inflammatory drugs (NSAIDs), widely used for relief of fever, pain and inflammation, act by inhibiting COX catalyzed biosynthesis of inflammatory mediators.
However, the therapeutic use of classical NSAIDs is associated with well-known side effects at the gastrointestinal level (mucosal damage, bleeding) and, less frequently, at the renal level.
Two decades after the discovery of COX isoforms, it was recognized that selective inhibition of COX-2 might be endowed with improved anti-inflammatory properties and reduced gastrointestinal toxicity profiles than classical NSAIDs.
Overall, these selective COX-2 inhibitors (coxibs) have fulfilled the hope of possessing reduced risk in gastrointestinal events, but unfortunately cardiovascular concerns regarding the use of these agents have emerged that led to the withdrawal of rofecoxib (Vioxx) and valdecoxib (Bextra) from the market in 2004 and 2005, respectively.
Ongoing safety concerns pertaining to the use of non-selective NSAIDs have spurred development of coxibs with improved safety profile.
……………………………………………………………………………………………..
STR4
cas no 1616882-93-9
mf……….C18 H11 F3 N2 O2
[1]​Benzopyrano[4,​3-​c]​pyrazol-​4(1H)​-​one, 3-​methyl-​1-​[4-​(trifluoromethyl)​phenyl]​-
 3-Methyl-1-(4-(trifluoromethyl)phenylchromeno[4,3-c]pyrazol-4(1H)-one
Full-size image (21 K)
Scheme 1.
Reagent and conditions: (a) Piperidine, rt, 20 min; (b) ArNHNH2, EtOH, reflux, 5 h; (c) K2CO3, acetone, reflux, 24 h.
COMPD IS
3bR1=HR2= H4-CF3-C6H490
3-Methyl-1-(4-(trifluoromethyl)phenylchromeno[4,3-c]pyrazol-4(1H)-one (3b):
White solid; yield 90%; mp: 224–225 °C;
1H NMR (CDCl3, 400 MHz): δ ppm 7.89 (d, 2H, J = 8.32 Hz, Ar-H), 7.73 (d, 2H, J = 8.24 Hz, Ar-H), 7.45–7.52 (m, 2H, H-6, H-7), 7.16 (dd, 1H, J = 1.4, 8.2 Hz, H-9), 7.10 (td, 1H, J = 1.56, 7.38 Hz, H-8), 2.69 (s, 3H, CH3);
13C NMR (CDCl3, 100 MHz): δ ppm 157.7, 153.3, 151.5, 142.3, 141.8, 131.9, 127.2, 127.1, 127.0, 124.0, 122.2, 118.3, 111.5, 107.1, 12.8;
HRMS (ESI) m/z: Calcd for C18H11F3N2O2Na [M + Na]+ 367.0670; found 367.0676.
Synthetic Communications (2014), 44(13), 1914-1923
DOI:
10.1080/00397911.2013.879184
Jagdeep Grovera, Somendu Kumar Roya & Sanjay Madhukar Jachaka*
pages 1914-1923

Abstract

Unprecedented cyclization was observed during N-sulfonylation of 3-[1-(phenylhydrazono)-ethyl]-chromen-2-one in pyridine, affording 3-methyl-1-phenylchromeno[4,3-c]pyrazol-4(1H)-ones. To avoid use of noxious pyridine, reaction was tried in different basic conditions and the best results were obtained with potassium carbonate in acetone. A wide range of substrates bearing either electron-donating or electron-withdrawing substituents on phenylhydrazine ring were compatible with the developed methodology. Rapid access of starting material, 3-acetylcoumarin, excellent yields of products, and use of environmentally benign base and solvent for the cyclization make this strategy an efficient and convenient method for synthesis of 3-methyl-1-phenylchromeno[4,3-c]pyrazol-4(1H)-ones.
STR4
Methyl-1-(4-(trifluoromethyl)phenylchromeno[4,3-c]pyrazol-4(1H)-one (4b):
Whitesolid;
yield 90%; mp: 224–225 °C;

1H NMR (CDCl3, 400 MHz):δppm 
2.69 (s, 3H, CH3),
7.10(td, 1H,J= 1.56, 7.38 Hz, H-8),
7.16 (dd, 1H,J= 1.4, 8.2 Hz, H-9),
7.45–7.52 (m, 2H, H-6, H-7),
7.73 (d, 2H,J= 8.24 Hz, Ar-H),
7.89 (d, 2H,J= 8.32 Hz, Ar-H);





13C NMR (CDCl3, 100MHz):
δppm
12.8, 
107.1, 
111.5, 
118.3, 
122.2, 
124.0,
127.0, 
127.1, 
127.2, 
131.9, 
141.8, 
142.3,
151.5, 
153.3, 
157.7;




HRMS (ESI)m/z: Calcd for C18H11F3N2O2Na [M + Na]+367.0670; found367.0676.


 3-Methyl-1-(4-(trifluoromethyl)phenylchromeno[4,3-c]pyrazol-4(1H)-one
STR4


SEE BELOW  1H NMR, 13CNMR, AND MASS SPEC



STR2



13C NMR


STR2

MASS
STR3
References
1. Jones, G.; Willett, P.; Glen, R. C.; Leach, A. R.; Taylor, R. J. Mol. Biol. 1997, 267, 727.
2. Bernstein, F. C.; Koetzle, T. F.; Williams, G. J. B.; Meyer, E. F.; Brice, M. D.; Rodgers, J. R.; Kennard, O.; Shimanouchi, T.; Tasumi, M. J. Mol. Biol. 1977, 112, 535.

Tuesday 23 September 2014

Your sister will teach you spectroscopy..3 ACETYL COUMARIN


 




3 ACETYL COUMARIN
CAS 3949-36-8
Synonym Name:
3-Acetyl-2H-chromen-2-one; 2H-1-benzopyran-2-one,
3-acetyl-; 3-acetyl-chromen-2-one
Synthesis Reference:
Monatshefte fur Chemie, 121, p. 85, 1990
H1 NMR Spectrum
Liu, Jinbing; Wu, Fengyan; Chen, Lingjuan; Zhao, Liangzhong; Zhao, Zibing; Wang, Min; Lei, Sulan
Food Chemistry, 2012 ,  vol. 135,  4  pg. 2872 - 2878

1H NMR, 400 MHZ
chloroform-d1
1H NMR (400 MHz, CDCl3):
δ 8.49 (s, 1H, C=CH),
7.65-7.63 (m, 2H, Ph-H),
7.37-7.32 (m, 2H, Ph-H),
2.71 (s, 3H, CH3)


13 C NMR
(100 MHz, CDCl3)
δ 195.41 (1C),  C=O OF ACETYL
159.17 (1C), C=O OF COUMARIN
155.27 (1C), ARC-O-C=O
147.39 (1C),
134.33 (1C),
130.17 (1C),
124.92 (1C),
124.48 (1C),

118.20 (1C),
116.63 (1C),
30.49 (1C)    -CH3

IR (KBr): 3078, 3026,
1723,  C=O
1675, 1598, 1556, 1441, 1406, 1351, 1297, 1220, 1198, 1162, 1098, 967, 762 cm-1