Alpha-glucosidase inhibitory constituents from Cuscuta reflexa

Two new compounds, 7'-(3',4'-dihydroxyphenyl)-N-[(4-methoxyphenyl)ethyl]propenamide (4), and 7'-(4'-hydroxy,3'-methoxyphenyl)-N-[(4-butylphenyl)ethyl]propenamide (5) have been isolated from Cuscuta reflexa along with five known compounds, 6,7-dimethoxy-2H-1-benzopyran-2-one (1), 3-(3,4-dihydroxyphenyl)-2-propen-1-ethanoate (2), 6,7,8-trimethoxy-2H-1-benzopyran-2-one (3), 3-(4-O-beta-D-glucopyranoside-3,5-dimethoxyphenyl)-2-propen-1-ol (6), 2-(3-hydroxy-4-methoxyphenyl)-3,5-dihydroxy-7-O-beta-D-glucopyranoside-4H-1-benzopyrane-4-one (7), reported for the first time from this species. Structures of these compounds were determined by spectral analysis. These compounds showed strong inhibitory activity against alpha-glucosidase.     

A μ(1,1)- or μ(1,3)-carboxylate bridge makes the difference in the magnetic properties of dinuclear Mn(II) compounds

Six new dinuclear Mn(II) compounds with carboxylate bridges have been synthesized and characterized by X-ray diffraction: [{Mn(phen)(2)}(2)(μ-RC(6)H(4)COO)(2)](ClO(4))(2) with R = 2-Cl (1), 2-CH(3) (2), 3-Cl (3), 3-CH(3) (4), 4-Cl (5) and 4-CH(3) (6). Compounds 1 and 2 show two μ(1,3)-carboxylate bridges in a syn-anti mode while compounds 3-6 present a very uncommon coordination mode of the carboxylate ligand: the μ(1,1)-bridge. The magnetic properties of these compounds are very sensitive to the bridging mode of the carboxylate ligands. While compounds 1 and 2 (μ(1,3)-bridge) display antiferromagnetic interactions, with J values of -1.41 and -1.66 cm(-1), respectively, compounds 3-6 (μ(1,1)-bridge) show ferromagnetic interactions, with J values of 1.01, 0.98, 1.04 and 1.06 cm(-1), respectively. It is worth noting that compounds 3-6 are the first of their class to be magnetically characterized. The EPR spectra at 4 K for compounds with antiferromagnetic coupling (1 and 2) are more complex than those for compounds with a ferromagnetic interaction (3-6). Quite good simulations can be obtained with the ZFS parameters of the Mn(II) ion D(Mn) ~ 0.095 cm(-1) and E(Mn) ~ 0.025 cm(-1) for compounds 1 and 2 and D(Mn) ~ 0.060 cm(-1) and E(Mn) ~ 0.004 cm(-1) for compounds 3-6.     

Highly selective colorimetric and electrochemical Pb2+ detection based on TTF-pi-pyridine derivatives

[reaction: see text] The pyridineethenyl-substituted tetrathiafulvalene (TTF) compounds, 4-(4-pyridineethenyl)tetrathiafulvalene (1a) and 4,4'(5')-[bis-(4-pyridineethenyl)]tetrathiafulvalene (2a) together with the styryl-substituted TTF compounds, 4-styryltetrathiafulvalene (1b) and 4,4'(5')-bis-styryltetrathiafulvalene (2b), have been designed and synthesized. All these compounds exhibit strong absorption bands in the range of 370 to 550 nm, which are assigned to the intramolecular charge-transfer transition from the HOMO in TTF to the LUMO in the pyridyl or phenyl group. Compared to compounds 1b and 2b, the pyridineethenyl-substituted TTF compounds 1a and 2a show remarkable sensing and coordinating properties to Pb2+. With the addition of micromolar concentrations of Pb2+ to the solution, 1a or 2a displays dramatic changes in the UV-vis absorption spectrum, 1H NMR spectrum, and redox property.     

Cyano- and Nitro-containing Compounds from the Roots of Semiaquilegia adoxoides

Four cyano-containing compounds, (1E,4α,5β,6α)-4,5,6-trihydroxy-2-cyclohexen-l-ylideneacetonitrile (1), lithospermoside (2), 4-hydroxy-2-β-D-glucopyranosyl oxyphenylacetonitrile (3) and 4-[β-D-apiofuranosyl-(1→6)-O-β-D-glucopyranosyl oxy]phenylacetonitrile (4), and a nitro-containing one, 4-[β-D-xylopyranosyl-(1→6)-O-β-D-glucopyranosyloxy]-1-(2-nitroethyl)benzene (5), as well as eleven other types of compounds, were isolated from the roots of Semiaquilegia adoxoides. Their structures were elucidated mainly by spectroscopic methods. Among them, 1 and 4 are new isolated compounds. The cyano- and nitro-containing compounds are very rare in plants and their isolation from one traditional Chinese medicine is really interesting.     

Synthesis of new synthons for organofluorine compounds from halothane containing sulfur functional groups

To develop new synthons for the syntheses of organofluorine compounds, the treatment of Halothane, 2-bromo-2-chloro-1,1,1-trifluoroethane, (1) with 4-methylbenzenethiol (2) in the presence of sodium hydride gave 1-chloro-2,2,2-trifluoroethyl 4-methylphenyl sulfide (3), which was oxidized with m-chloroperbenzoic acid (m-CPBA) to the corresponding sulfoxide (4) and sulfone (5). Reaction of 3 and 5 with allyltributyltin in the presence of 2,2'-azobis(isobutyronitrile) (AIBN) gave 1-(trifluoromethyl)-3-butenyl compounds (9, 11). Sulfoxide 4 was decomposed in this condition. The treatment of 3 with allyltrimethylsilane in the presence of Lewis acids gave 1-(trifluoromethyl)-3-butenyl compounds (9) in good yield. This result suggests that 4-methylphenylthio substituent stabilizes the alpha-carbocation effectively, though the trifluoromethyl group destabilizes it strongly. Aromatic compounds similarly reacted with 3 in the presence of titanium(IV) chloride to give 2-aryl-1,1,1-trifluoro-2-(4-methylphenylthio)ethanes. Thus, sulfur compounds derived from Halothane were found to be useful new synthons for organofluorine compounds.     

Synthesis and search for compounds with hemostatic activity in the series of 4-(het)aryl-4-oxobut-2-enoic acid derivatives

New 4-aryl-2-(4-arylamino)-1-(piperazin-1-yl)but-2-ene-1,4-diones and 2-{[2-(3-R-adamantan-1-yl)-2-oxoethylidene]hydrazinyl}-4-(het)aryl-4-oxobut-2-enoic acids were synthesized and used to obtain water-soluble compounds. Their influence on the blood coagulation system was studied, which revealed compounds with a high hemostatic activity and a low acute toxicity. A relationship between structure and pharmacological effect of the synthesized compounds was established.     

Synthesis and characterisation of trigonal C2-chiral di- and tetra-substituted bis(oxazoline) alkyl zinc complexes and their reactivity towards protic reagents

A series of zinc(ii) alkyl complexes stabilised by the C(2)-chiral bis(oxazoline) ligand ((R(1),R(2))BOX, with R(1) = (4S)-tBu, R(2) = H (a); R(1) = (4S)-Ph, R(2) = H (b); R(1) = (4R)-Ph, R(2) = (5S)-Ph (c)), has been synthesised and structurally characterised. ((R(1),R(2))BOX)H ligands react with ZnEt(2) in toluene to give the heteroleptic three-coordinate compounds of ((R(1),R(2))BOX)ZnEt, 1a, 1b and 1c in high yield. However, when the addition of (BOX)H ligands (a-b) over ZnEt(2) is "uncontrolled", the formation of homoleptic four-coordinate compounds are favoured (2a-b), but not for the more sterically crowded ligand (c). The zinc-ethyl derivatives (1a-c) react readily with protic reagents such as acetic acid (HOAc) and methanol (MeOH). For compounds 1a-c a redistribution of ligands is observed leading preferentially to homoleptic compounds, except for the bulkier ligand c providing a three-coordinate complex identified as ((Ph,Ph)BOX)Zn(OMe), 4c. The reaction of acetylacetone (acacH) with compounds 1a-c leads straightforwardly to the more stable four-coordinate compounds corresponding to ((R(1),R(2))BOX)Zn(η(2)-acac), 5a-c. The potential of these compounds as initiators for the copolymerisation of epoxides with CO(2) was investigated.     

Synthesis and pharmacological evaluation of some 3-(4-methoxyphenyl)-2-substitutedamino-quinazolin-4(3H)-ones as analgesic and anti-inflammatory agents

A variety of novel 3-(4-methoxyphenyl)-2-substitutedamino-quinazolin-4(3H)-ones were synthesized by reacting the amino group of 2-hydrazino-3-(4-methoxyphenyl)-quinazolin-4(3H)-one with a variety of alkyl and aryl ketones. The starting material 2-hydrazino-3-(4-methoxyphenyl)-quinazolin-4(3H)-one was synthesized from 4-methoxyaniline. The title compounds were investigated for analgesic, anti-inflammatory and ulcerogenic index activities. While the test compounds exhibited significant activity, compounds 2-(1-methylpropylidene)-hydrazino-3-(4-methoxyphenyl)-quinazolin-4(3H)-one (A1), 2-(1-ethylpropylidene)-hydrazino-3-(4-methoxyphenyl)-quinazolin-4(3H)-one (A2) and 2-(1-methylbutylidene)-hydrazino-3-(4-methoxyphenyl)-quinazolin-4(3H)-one (A3) showed moderately more potent analgesic activity and the compound 2-(1-methylbutylidene)-hydrazino-3-(4-methoxyphenyl)-quinazolin-4(3H)-one (A3) showed moderately more potent anti-inflammatory activity when compared to the reference standard diclofenac sodium. Interestingly the test compounds showed only mild ulcerogenic potential when compared to aspirin.     

Diplatinum(III) complexes with four bridging 1-methylcytosinato nucleobases derived from a mononuclear trans-(NH3)2PtII complex and CuII

A heteronuclear complex of composition trans-[(NH(3))(2)Pt(N4-1-MeC(-)-N3)(2)Cu(H(2)O)(2)](ClO(4))(2) (1a), with 1-MeC(-) = 1-methylcytosinate, has been prepared and characterized by X-ray crystallography. 1a (Cu,Pt) is a linkage isomer of a previously described compound with the two metals inverted (Pt,Cu). The intermetallic distances are significantly different in the two types of compounds, 2.6109(9) A in 1a, yet 2.49-2.56 A in several forms of the linkage isomer. When heated in water in the presence of air, 1a is converted in low yield into diplatinum(III) compounds [(H(3)N)Pt(1-MeC(-)-N3,N4)(4)Pt(NH(3))](2+) (2a) and [(H(2)O)Pt(1-MeC(-)-N3,N4)(4)Pt(NH(3))](2+) (2b), which were crystallized as ClO(4)(-) salts. In a modified procedure a third representative of this group of diplatinum(III) compounds, [(O(2)N)Pt(1-MeC(-)-N3,N4)(4)Pt](+) (2c) was isolated. All three compounds contain the four bridging 1-MeC ligands in a head,tail,head,tail arrangement with Pt-Pt distances (2.4516(7)-2.4976(9) A) that are the shortest ones among diplatinum(III) compounds containing nucleobases.     

Isolation of toxic compounds from wild Phaeocystis globosa

Two new compounds, namely taenialactam C and globorin A (1 and 2), as well as six known compounds, cornoside (3), 2-phenylethyl-b-D-glucoside (4), 3-isopropyl-5-acetoxycyclohexene-2-one-1 (5), 4-methyl-phenol (6), 5-[(2S)-2-aminobutyl]-2-methyl-phenol (7), and 1-(4-methylphenyl)-1-propanone (8) were isolated from wild Phaeocystis globosa. The structures of the new compounds were established by detailed spectroscopic analysis and by comparison with spectral data of related known compounds. The structures of the known compounds were identified by comparing their spectroscopic data with those reported in the literature. This paper also reports toxicity properties of the eight compounds against the brine shrimp Artemia salina and juvenile Epinephelus akaara fish. Some of these compounds showed significant lethality on the brine shrimp A. salina and the juvenile E. akaara fish.     

Synthesis and characterization of Ru2(DMBA)4X2 (X = CN, N3, N(CN)2, I): controlling structural, redox, and magnetic properties with axial ligands

Metathesis reactions between Ru(2)(DMBA)(4)Cl(2) (DMBA = N,N'-dimethylbenzamidinate) and MX (M = Na and K) yielded bis-adduct derivatives Ru(2)(DMBA)(4)X(2) (X = CN (1), N(3) (2), N(CN)(2) (3)). Metathesis reactions between Ru(2)(DMBA)(4)(NO(3))(2) and KI resulted in Ru(2)(DMBA)(4)I(2) (4). Compound 1 is diamagnetic, while compounds 2-4 are paramagnetic (S = 1). Both compounds 1 and 2 undergo two reversible one-electron processes, an oxidation and a reduction, while compound 3 features a quasireversible reduction. Single-crystal X-ray diffraction studies revealed that the Ru-Ru bond lengths are 2.4508(9), 2.3166(7), 2.304[1], and 2.328(1) A for compounds 1-4, respectively. Structural and electrochemical data clearly indicate that the axial ligands impart a significant influence on the electronic structures of diruthenium species.     

Syntheses, structures, and nonlinear optical properties of heteroselenometallic W-Se-Ag cluster compounds containing phosphine ligands

Treatment of [Et4N]2[WSe4] with a 1:1 mixture of AgNO3 and PCy3 (Cy = cyclohexyl) in the absence of iodide afforded a linear trinuclear compound [(mu-WSe4)(AgPCy3)2] (1). A similar reaction in the presence of iodide gave rise to the isolation of the cubanelike compound [(mu3-WSe4)Ag3(PCy3)3(mu3-I)] (2). Treatment of [Et4N]2[WSe4] with AgI in the presence of bidentate phosphine ligands bis(diphenylphosphino)amine (dppa) and bis(diphenylphosphino)methane (dppm) afforded the tetranuclear compounds [(mu3-WSe4)Ag3(mu-I)(mu-dppa)2] (3) and [(mu3-WSe4)Ag3(mu3-I)(mu-dppm)2] (4), respectively, which exhibit an open butterfly configuration. A novel hexanuclear cluster compound [(mu3-WSe4)2Ag4(mu-dppm)3] (5) was obtained from interaction of [Et4N]2[WSe4] with AgNO3 and dppm in the absence of iodide source. The above cluster compounds are electrically neutral and air-stable in both solution and the solid state and have been characterized by electronic, infrared, mass, and NMR spectroscopies. The solid-state structures of five cluster compounds have been established by X-ray crystallography. The nonlinear optical properties of compounds 4 and 5 were examined by z-scan techniques with 7 ns pulses at 532 nm. The optical limiting effects of compounds 1, 2, 4, and 5 were determined and compared with related argentoselenometallic compounds.     

Polyyn-diyls capped by diruthenium termini: a new family of carbon-rich organometallic compounds and distance-dependent electronic coupling therein

Polyyn-diyls capped by Ru(2)(ap)(4) termini (ap = 2-anilinopyridinate), that is, [Ru2(ap)4](mu-C,C'-C2m)[Ru2(ap)4] (compounds 1-5 with m = 1-4 and 6), were synthesized through either a metathesis reaction between Ru2(ap)4Cl and LiC(2m)Li or a Glaser homocoupling reaction of Ru2(ap)4(CmH) under Eglinton/Hay conditions. X-ray diffraction studies of compounds 2 and 4 revealed both the linear rigid rod topology of these compounds and the fine structural details about the Ru2 cores and polyyn-diyl chains. Cyclic and differential pulse voltammetric (CV and DPV) measurements and spectroelectrochemical studies show that reduced and oxidized forms of 1, 2, 4, and 5 are donor-acceptor systems in which the Ru2 termini are coupled to varying degrees depending upon the length of the polyyn-diyl bridge.     

Syntheses and Crystal Structures of 9-Ethyl-1,3,6,8-tetra-aryl-9H-carbazole Compounds

The title compounds 9-ethyl-1,3,6,8-tetra-p-tolyl-9H-carbazole (1) and 9-ethyl-1,3,6,8-tetrakis-(4-fluoro-phenyl)-9H-carbazole (2) were synthesized and characterized by single-crystal X-ray diffraction. Thereinto, the crystal structures of compounds 1 and 2 were composed by asymmetry units. The ratio of compounds 1 and 2 to the solvent molecule cyclohexane (CYH) is 4/3. X-ray analysis reveals that the 1,3,6,8-phenyl groups are distorted at large angles relative to the planar carbazole ring. Furthermore, the luminescent and thermal properties of 1 and 2 have also been investigated. It can be seen that thermal stability of compound 1 with p-tolyl is better than that of 2 with 4-fluoro-phenyl. Fluorescence spectra analysis showed that compounds 1 and 2 have strong UV emission.     

Five new phenylethanoid glycosides from the whole plants of Lamium purpureum L

Five new phenylethanoid glycosides, lamiusides A (1), B (2), C (3), D (4) and E (5), were isolated from the whole plants of Lamium purpureum L. (Labiatae) together with seven known compounds (6-12). On the basis of chemical and spectral analyses, the structures of the new compounds were elucidated to be 2-(3,4-dihydroxyphenyl)ethyl-O-beta-D-galactopyranosyl-(1-->2)-alpha-L-rhamnopyranosyl-(1-->3)-(4-O-trans-caffeoyl)-beta-D-glucopyranoside (1), 2-(3,4-dihydroxyphenyl)ethyl-O-beta-D-galactopyranosyl-(1-->2)-alpha-L-rhamnopyranosyl-(1-->3)-(4-O-trans-feruloyl)-beta-D-glucopyranoside (2), 2-(3,4-dihydroxyphenyl)ethyl-O-beta-D-galactopyranosyl-(1-->2)-alpha-L-rhamnopyranosyl-(1-->3)-(6-O-trans-caffeoyl)-beta-D-glucopyranoside (3), 2-(3,4-dihydroxyphenyl)-R,S-methoxy-ethyl-O-beta-D-galactopyranosyl-(1-->2)-alpha-L-rhamnopyranosyl-(1-->3)-(4-O-trans-caffeoyl)-beta-D-glucopyranoside (4) and 2-(3-hydroxy-4-methoxyphenyl)ethyl-O-alpha-L-rhamnopyranosyl-(1-->3)-beta-D-glucopyranosyl-(1-->6)-(4-O-cis-feruloyl)-beta-D-glucopyranoside (5). In addition, the radical-scavenging activities of compounds 1-4 on 1,1-diphenyl-2-picrylhydrazyl radical were examined.     

Pharmacological activities of the prenylcoumarins, developed from folk usage as a medicine of Peucedanum japonicum THUNB

In connection with the chemical structure of coumarin 1 (a mixture of acetylangeloylkhellactone and acetyltigloylkhellactone), a compound isolated from Peucedanum japonicum THUNB., we synthesized eight coumarin compounds (3-10) and performed pharmacological studies on these nine compounds, as well as on another coumarin, praeruptorin A (= Pd-Ia) (2), a compound isolated from Peucedanum praeruptorum DUNN. We studied the effects of compounds 1-5 on isolated smooth muscle and of compounds 1-10 on the cardiovascular system. These compounds showed dose-related antagonistic effects on histamine- and Ca(2+)-induced contractions in smooth muscle and the potencies were in the order 2 greater than 1 greater than seselin (3) greater than xanthyletin (4) = 2.2.10-trimethyl-2H,8H-benzo[1,2-b: 3,4-b']dipyran-8-one (5). All the compounds except 7-geranyloxy-4-methylcoumarin (10) produced a dose-related increase in vertebral, carotid and femoral blood flow. Compounds 1, 5, and 4-methyl-7-(3-methyl-2-butenyloxy)coumarin (8) caused an increase in blood pressure, but 3 and 4 caused a slight decrease. Compounds 2, 3, 4, 5, and 8 increased heart rate. Jatamansinone (6) and jatamansinol (7) caused only slight changes in blood pressure. All the compounds except 10 increased heart rate. Compound 1 also increased blood flow in the cerebral cortex. Thus, compound 1 was confirmed to have an inhibitory effect on contraction in isolated smooth muscle and an action increasing arterial blood flow. Among the compounds tested in this study, 3, as well as 6 and 7 synthesized on the basis of 3, showed actions similar to those of Ca2+ blockers and some compounds had papaverine-like activities.(ABSTRACT TRUNCATED AT 250 WORDS)     

M2(hpp)4Cl2 and M2(hpp)4, where M = Mo and W: preparations, structure and bonding, and comparisons with C2, C2H2, and C2Cl2 and the hypothetical molecules M2(hpp)4(H)2

The reaction between M(2)Cl(2)(NMe(2))(4), where M = Mo or W, and Hhpp (8 equiv) in a solid-state melt reaction at 150 degrees C yields the compounds M(2)(hpp)(4)Cl(2) 1a (M = Mo) and 1b (M = W), respectively, by the elimination of HNMe(2) [hpp is the anion derived from deprotonation of 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine, Hhpp]. Purification of 1a and 1b is achieved by sublimation of the excess Hhpp and subsequent recrystallization from either CH(2)Cl(2) or CHCl(3) (or CDCl(3)). By single-crystal X-ray crystallography, the structures of 1a and 1b are shown to contain a central paddlewheel-like M(2)(hpp)(4) core with Mo-Mo = 2.1708(8) A (from CH(2)Cl(2)), 2.1574(5) A (from CDCl(3)), W-W = 2.2328(2) A (from CDCl(3)), and M-N = 2.09(1) (av) A. The Cl ligands are axially ligated (linear Cl-M-M-Cl) with abnormally long M-Cl bond distances that, in turn, depend on the presence or absence of hydrogen bonding to chloroform. The quadruply bonded compounds M(2)(hpp)(4), 2a (M = Mo), and 2b (M = W), can be prepared from the reactions between 1,2-M(2)R(2)(NMe(2))(4) compounds, where R = (i)()Bu or p-tolyl, and Hhpp (4 equiv) in benzene by ligand replacement and reductive elimination. The compounds 2a and 2b are readily oxidized, and in chloroform they react to form 1a and 1b, respectively. The electronic structure and bonding in the compounds 1a, 1b, 2a, and 2b have been investigated using gradient corrected density functional theory employing Gaussian 98. The bonding in the M-M quadruply bonded compounds, 2a and 2b, reveals M-M delta(2) HOMOs and extensive mixing of M-M pi and nitrogen ligand lone-pair orbitals in a manner qualitatively similar to that of the M(2)(formamidinates)(4). The calculations indicate that in the chloride compounds, 1a and 1b, the HOMO is strongly M-Cl sigma antibonding and weakly M-M sigma bonding in character. Formally there is a M-M triple bond of configuration pi(4)sigma(2), and the LUMO is the M-M delta orbital. An interesting mixing of M-M and M-Cl pi interactions occurs, and an enlightening analogy emerges between these d(4)-d(4) and d(3)-d(3) dinuclear compounds and the bonding in C(2), C(2)H(2), and C(2)Cl(2), which is interrogated herein by simple theoretical calculations together with the potential bonding in axially ligated compounds where strongly covalent M-X bonds are present. The latter were represented by the model compounds M(2)(hpp)(4)(H)(2). On the basis of calculations, we estimate the reactions M(2)(hpp)(4) + X(2) to give M(2)(hpp)(4)X(2) to be enthalpically favorable for X = Cl but not for X = H. These results are discussed in terms of the recent work of Cotton and Murillo and our attempts to prepare parallel-linked oligomers of the type [[bridge]-[M(2)]-](n)().     

3-取代-6-吡唑基-1,2,4-三唑并[3,4-b]-1,3,4-噻二唑类衍生物的合成及生物活性

将5-取代吡唑-3-甲酸乙酯1位甲基化,经水解反应得到3种中间体1-甲基-5-取代1H-吡唑-3-甲酸（2a~2c）;以不同取代的羧酸为原料经一系列反应合成6种中间体3-取代4-氨基-5-巯基-1,2,4-均三唑（3a~3f）;将中间体（2a~2c）和（3a~3f）在三氯氧磷条件下反应,合成出18种1,2,4-三唑并[3,4-b]-1,3,4-噻二唑类化合物(4a~4r),均未见文献报道。 通过IR、1H NMR、13C NMR和元素分析表征了化合物结构。 初步的生物活性测试结果显示,所合成的化合物均表现出不同程度的生长素活性和抑菌活性。 并选取抑菌活性较好的两个化合物进行抗菌药物最低抑菌浓度(MIC)的测定。     

Heterocyclic compounds from 3,3-dimercapto-1-aryl-2-propen-1-ones. Note 3. Condensation with N-methyl-o-phenylenediamine and N-benzyl-o-phenylenediamine

Two seven-membered ring compounds and three five-membered ring compounds were obtained by reaction in hot xylene of 3,3-dimercapto-l-phenyl-2-propen-1-one (1) with N-alkyl-o-phenylenediamines (2) . Compounds isolated were the 4-phenyl-5-alkyl-1,5-dihydro-2H-1,5-benzodiazepine-2-thiones (3) the 1-alkyl-4-phenyl-1,3-dihydro-2H-1,5-benzodiazepine-2-thiones (4) , the 1-alkyl-2-phenacylbenzimidazoles (5) , the 1-alkyl-2-phenylbenzimidazoles (6) and the 1-alkyl-2-methylbenzimidazoles (7) . The structures of these compounds were elucidated from their chemical reactivity and their nmr and ir spectra.