Cycloalkanone-Based Threo and Erythro Aldols as Supramolecular Synthons in Crystal Engineering

2003 ◽  
Vol 3 (1) ◽  
pp. 25-34 ◽  
Author(s):  
Masato Kitamura ◽  
Keiji Nakano
Keyword(s):  
Crystal Engineering ◽  
Supramolecular Synthons

scholarly journals Two-dimensional crystal engineering using halogen and hydrogen bonds: towards structural landscapes

2017 ◽  
Vol 8 (5) ◽  
pp. 3759-3769 ◽  
Author(s):  
Arijit Mukherjee ◽  
Joan Teyssandier ◽  
Gunther Hennrich ◽  
Steven De Feyter ◽  
Kunal S. Mali
Keyword(s):  
Hydrogen Bonds ◽  
Crystal Engineering ◽  
Two Dimensional ◽  
Supramolecular Synthons ◽  
Solid Interface ◽  
Dimensional Crystal

We apply the concepts of supramolecular synthons and structural landscapes to 2D crystallization at the solution–solid interface.

Supramolecular Synthons in Crystal Engineering. 3. Solid State Architecture and Synthon Robustness in Some 2,3-Dicyano-5,6-dichloro-1,4-dialkoxybenzenes1

1996 ◽  
Vol 118 (17) ◽  
pp. 4085-4089 ◽  
Author(s):  
D. Shekhar Reddy ◽  
Yuri E. Ovchinnikov ◽  
Oleg V. Shishkin ◽  
Yuri T. Struchkov ◽  
Gautam R. Desiraju
Keyword(s):  
Solid State ◽  
Crystal Engineering ◽  
Supramolecular Synthons

Supramolecular synthons in crystal engineering. Structure simplification, synthon robustness and supramolecular retrosynthesis

1996 ◽  
pp. 401 ◽  
Author(s):  
Venkat R. Thalladi ◽  
B. Satish Goud ◽  
Vanessa J. Hoy ◽  
Frank H. Allen ◽  
Judith A. K. Howard ◽  
...  
Keyword(s):  
Crystal Engineering ◽  
Supramolecular Synthons ◽  
Engineering Structure ◽  
Structure Simplification

Transferability of Multipole Charge Density Parameters for Supramolecular Synthons: A New Tool for Quantitative Crystal Engineering

2011 ◽  
Vol 11 (2) ◽  
pp. 616-623 ◽  
Author(s):  
Venkatesha R. Hathwar ◽  
Tejender S. Thakur ◽  
Tayur N. Guru Row ◽  
Gautam R. Desiraju
Keyword(s):  
Charge Density ◽  
Crystal Engineering ◽  
Supramolecular Synthons

scholarly journals Binary and ternary cocrystals of sulfa drug acetazolamide with pyridine carboxamides and cyclic amides

IUCrJ ◽  
2016 ◽  
Vol 3 (2) ◽  
pp. 152-160 ◽  
Author(s):  
Geetha Bolla ◽  
Ashwini Nangia
Keyword(s):  
Single Crystals ◽  
Crystal Engineering ◽  
Design Strategy ◽  
Supramolecular Synthons ◽  
Sulfa Drug ◽  
Sulfonamide Drug ◽  
Solution Crystallization ◽  
Shape Match ◽  
Engineering Study ◽  
Novel Design

A novel design strategy for cocrystals of a sulfonamide drug with pyridine carboxamides and cyclic amides is developed based on synthon identification as well as size and shape match of coformers. Binary adducts of acetazolamide (ACZ) with lactams (valerolactam and caprolactam, VLM, CPR), cyclic amides (2-pyridone, labeled as 2HP and its derivatives MeHP, OMeHP) and pyridine amides (nicotinamide and picolinamide, NAM, PAM) were obtained by manual grinding, and their single crystals by solution crystallization. The heterosynthons in the binary cocrystals of ACZ with these coformers suggested a ternary combination for ACZ with pyridone and nicotinamide. Novel supramolecular synthons of ACZ with lactams and pyridine carboxamides are reported together with binary and ternary cocrystals for a sulfonamide drug. This crystal engineering study resulted in the first ternary cocrystal of acetazolamide with amide coformers, ACZ–NAM–2HP (1:1:1).

scholarly journals Modularity and three-dimensional isostructurality of novel synthons in sulfonamide–lactam cocrystals

IUCrJ ◽  
2015 ◽  
Vol 2 (4) ◽  
pp. 389-401 ◽  
Author(s):  
Geetha Bolla ◽  
Sudhir Mittapalli ◽  
Ashwini Nangia
Keyword(s):  
Hydrogen Bonding ◽  
Crystal Structures ◽  
Functional Groups ◽  
Crystal Engineering ◽  
Three Dimensional ◽  
Sulfa Drugs ◽  
Level Control ◽  
Supramolecular Synthons ◽  
The Individual ◽  
Sulfonamide Group

The design of novel supramolecular synthons for functional groups relevant to drugs is an essential prerequisite for applying crystal engineering in the development of novel pharmaceutical cocrystals. It has been convincingly shown over the past decade that molecular level control and modulation can influence the physicochemical properties of drug cocrystals. Whereas considerable advances have been reported on the design of cocrystals for carboxylic acids and carboxamide functional groups, the sulfonamide group, which is a cornerstone of sulfa drugs, is relatively unexplored for reproducible heterosynthon-directed crystal engineering. The occurrence of synthons and isostructurality in sulfonamide–lactam cocrystals (SO2NH2...CONH hydrogen bonding) is analyzed to define a strategy for amide-type GRAS (generally recognized as safe) coformers with sulfonamides. Three types of supramolecular synthons are identified for the N—H donor of sulfonamide hydrogen bonding to the C=O acceptor of amide. Synthon 1: catemer synthonC21(4) chain motif, synthon 2: dimer–cyclic ring synthonR22(8)R42(8) motifs, and synthon 3: dimer–catemer synthon ofR22(8)C11(4)Dnotation. These heterosynthons of the cocrystals observed in this study are compared with the N—H...O dimerR22(8) ring andC(4) chain motifs of the individual sulfonamide structures. The X-ray crystal structures of sulfonamide–lactam cocrystals exhibit interesting isostructurality trends with the same synthon being present. One-dimensional, two-dimensional and three-dimensional isostructurality in crystal structures is associated with isosynthons and due to their recurrence, novel heterosynthons for sulfonamide cocrystals are added to the crystal engineer's toolkit. With the predominance of sulfa drugs in medicine, these new synthons provide rational strategies for the design of binary and potentially ternary cocrystals of sulfonamides.

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