Ethyl 2-[4,5-bis-(butyl-sulfan-yl)-1,3-dithiol-2-yl-idene]-1,3-dithiolo[4,5-c]pyrrole-4-carboxyl-ate.

In the title mol-ecule, C(19)H(25)NO(2)S(6), the butyl chains are each disordered over two conformations in a 0.689 (10):0.311 (10) ratio. In the crystal, pairs of N-H⋯O hydrogen bonds link mol-ecules into centrosymmetric dimers. Short S⋯S contacts of 3.553 (4) Šare observed.

1-(1,3-Benzothia-zol-2-yl)-3-phenyl-2-pyrazoline.

In the title compound, C(16)H(13)N(3)S, the pyrazoline ring forms dihedral angles of 6.89 (14) and 4.96 (11)° with the benzene ring and the benzothia-zole group, respectively. In the crystal, weak C-H⋯N inter-actions link the mol-ecules into chains extending along the b-axis direction.

2,3-Bis(ethyl-sulfan-yl)-1,4,5,8-tetra-thia-fulvalene-6,7-dicarbonitrile.

In the title compound, C(12)H(10)N(2)S(6), all non-H atoms, except for those in the ethyl groups, lie in the same non-crystallographic plane, with a r.m.s. deviation of 0.0366 (5) Å. In the crystal structure, mol-ecules are linked through weak C-H⋯N hydrogen bonds between methyl and cyano groups, forming centrosymmetric dimers. The dimers are arranged along the a axis, due to inter-molecular N⋯S [3.337 (4) Å] inter-actions.

Methyl 3-(1H-indol-3-yl)propano-ate.

The mol-ecule of the title compound, C(12)H(13)NO(2), adopts an essentially planar conformation (r.m.s. deviation = 0.057 Å). In the crystal, the mol-ecules are linked by inter-molecular N-H⋯O hydrogen bonds, generating chains along [201].

(E)-Methyl 3-(1H-indol-2-yl)acrylate.

The title compound, C(12)H(11)NO(2), is close to being planar (r.m.s. deviation for the non-H atoms = 0.033 Å). In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds, generating C(7) chains running along the b axis. A weak C-H⋯O interaction helps to establish the packing.

(E)-Methyl 3-(1H-indol-3-yl)acrylate.

In the title compound, C(12)H(11)NO(2), the indole and methyl acrylate mean planes are inclined at an angle of 10.6 (1)°. In the crystal, N-H⋯π inter-actions link mol-ecules into chains along [010] and weak inter-molecular C-H⋯O hydrogen bonds further consolidate the crystal packing.

2-[4,5-Bis(butyl-sulfan-yl)-1,3-dithiol-2-yl-idene]-5-methyl-5H-1,3-dithiolo[4,5-c]pyrrole-4-carbaldehyde.

In the title compound, C(18)H(23)NOS(6), the dithiol-opyrrole ring is almost planar [r.m.s. deviation = 0.044 (3) Å] and makes a dihedral angle of 25.11 (7)° with the dithiole ring. In the crystal, pairs of neighboring mol-ecules are connected by weak inter-molecular C-H⋯O inter-actions. These dimers are further linked into a chain along [110] by C-H⋯O inter-actions.

6,7-Bis(methyl-sulfan-yl)-2,3-[(3,6,9-trioxaundecane-1,11-di-yl)bis-(sulfanediylmethyl-ene)]-1,4,5,8-tetra-thia-fulvalene.

In the title compound, C(18)H(26)O(3)S(8), the two five-membered rings exhibit envelope conformations. The two S atoms in the 17-membered macrocycle deviate from the plane of the fused five-membered ring by 1.429 (3) and -1.434 (3) Šin opposite directions.

4,6,7,9,10,12,13,15,16,18-Decahydro-1,3-dithiolo[4,5-l][1,4,7,10,15]trioxadithia-cyclo-hepta-decine-2-thione.

The title compound, C(13)H(20)O(3)S(5), is bis-ected by a crystallographic twofold rotation axis, which relates the two halves of the mol-ecule to one another: one S, one C and one O atom lie on the axis. The thione S atom lies in the plane of the five-membered rings with an r.m.s. deviation of 0.0042 (5) Å. Parts of the 17-membered macrocycle were refined using a two-part disorder model [occupancies of 0.553 (14) and 0.447 (14)]. There are no noteworthy inter-molecular inter-actions.

2,3-(3,6,9-Trioxaundecane-1,11-diyl-disulfan-yl)-1,4,5,8-tetra-thia-fulvalene-6,7-dicarbonitrile.

In the title compound, C(16)H(16)N(2)O(3)S(6), the two five-membered rings form a dihedral angle of 7.86 (9)°. Weak C-H⋯N hydrogen bonds link the mol-ecules to form a chain along c; the chains are further connected by weak C-H⋯O hydrogen bonds to form a three-dimensional supra-molecular network.

13-[4,5-Bis(methyl-sulfan-yl)-1,3-dithiol-2-yl-idene]-6-oxa-3,9,12,14-tetra-thia-bicyclo-[9.3.0]tetra-dec-1(11)-ene.

In the title mol-ecule, C(14)H(18)OS(8), one O atom, two S atoms and six C atoms form an 11-membered ring with a chair-like conformation; the planes of the two five-membered rings connected by a carbon-carbon double bond form a dihedral angle of 29.97 (11)°. In the crystal, pairs of weak inter-molecular C-H⋯S hydrogen bonds link two mol-ecules into inversion dimers.

2,3-[(3,6-Dioxaoctane-1,8-diyl)bis(sul-fanediylmethylene)]-6,7-bis(methylsulfanyl)-1,4,5,8-tetra-thia-fulvalene.

In the title mol-ecule, C(16)H(22)S(8)O(2), two S atoms, two O atoms and ten C atoms form a 14-membered ring with a boat conformation. In the crystal, C-H⋯O hydrogen bonds link the mol-ecules into dimers which are further connected into a chain along the a axis by C-H⋯S hydrogen bonds.

4,6,7,9,10,12-Hexahydro-1,3-dithiolo[4,5-f][1,4,9]oxadithia-cyclo-undecine-2-thione.

In the title mol-ecule, C(9)H(12)S(5)O, the five-membered ring and attached S atom are essentially coplanar [mean deviation from the mean plane = 0.020 (1) Å]. The two S atoms belonging to the macrocycle deviate from this plane by 1.005 (1) and 1.337 (2) Å. In the crystal, π-π inter-actions link the mol-ecules into centrosymmetric dimers with a short distance of 3.753 (5) Šbetween the centroids of the five-membered rings.

4,6,7,9,10,12,13,15-Octa-hydro-2H-1,3-dithiolo[4,5-i][1,4,7,12]dioxadithia-cyclo-tetra-decine-2-thione.

In the title mol-ecule, C(11)H(16)O(2)S(5), the two S atoms from the macrocycle are situated on opposite sides of the mean plane of the five-membered ring, deviating from it by 1.288 (3) and 1.728 (3) Å. In the crystal, weak inter-molecular C-H⋯S and C-H⋯O hydrogen bonds link the mol-ecules into layers parallel to (100). The crystal studied was a racemic twin.

Methyl 2,3-(3,6,9-trioxaundecane-1,11-diyldithio)-1,4,5,8-tetra-thia-fulvalene-6-carboxyl-ate.

In the title mol-ecule, C(16)H(20)O(5)S(6), the two five-membered rings form a dihedral angle of 4.7 (3)°. The crystal packing exhibits weak inter-molecular C-H⋯O hydrogen bonds, which link the mol-ecules into chains propagating in [10], and π-π inter-actions, indicated by the short distances [3.756 (5) Å] between the centroids of five-membered rings from mol-ecules related by translation along the b axis.

Design, Synthesis and Structure-Activity Relationship Studies of Novel 4 (1-adamantyl) Phenyl Analogues as HIF-1α Inhibitors.

Hypoxia inducible factor-1 (HIF-1) is a key mediator during cancer cells to adapt tumor hypoxic condition. In this study, a series of adamantane-based compounds were synthesized and evaluated as potential inhibitors of HIF-1α. Examination of their structure-activity relationship (SAR) identified the adamantane-containing indole derivative 20a as a potent inhibitor of HIF-1α in Hep3B cell lines under tumor hypoxia (IC50 = 0.02 µM). The study herein may provide valuable information for the development of novel therapeutics against cancer and tumor angiogenesis.