the present invention relates to non - brominated , partially alkylated pyrogallol calixarene type compounds and derivatives thereof . the compounds according to the invention may be prepared by selective alkylation of the cyclised calixarene type compound of the following formula the difficulties associated with selective alkylation of cyclised calixarenes of the above formula will be appreciated by those skilled in the art . in particular , in the above cyclised calixarene there are twelve hydroxyl groups . esterification can take place at twelve reaction sites . some of the reaction sites are less reactive than others due to possible steric hindrance . it will be appreciated by those skilled in the art that several of the hydroxyl groups in the non - alkylated calixarene are hindered which could prevent alkylation occurring at these positions . once the first alkyl group is alkylated the steric is hindrance is increased . thus it will be further appreciated by those skilled in the art that such steric hindrance may prevent total alkylation occurring unless vigorous conditions are applied such as , for example , stirring under reflux for 72 hours using a large excess of alkylating agent . thus following alkylation , the product can contain between 1 and 11 alkyl substituents . it will further be appreciated by those skilled in the art that partially alkylated compounds such as those described herein may be prepared by selective alkylation incorporating the use of well known protecting groups . table 1 shows the activity of compounds which were prepared in the following examples and tested . to pyrogallol ( 40 g , 0 . 317 mole ) in absolute ethanol ( 180 cm 3 ) was added p - fluorobenzaldehyde ( 39 g , 0 . 317 mole ) and 37 % hcl ( aq .) ( 46 . 5 cm 3 ). the reaction mixture was stirred under reflux for five hours . after cooling , the solid precipitate was collected by filtration and washed with ethanol : water ( 4 : 1 ). the crude brown solid was then slurried under reflux in methanol , cooled , filtered and washed with cold methanol to yield 39 g ( 53 %) of a grey / white solid . ( ii ) pyrogallol calixarene ( 14 g , 0 . 015 mole ) was treated with potassium carbonate ( 12 . 44 g , 0 . 09 mole ) and ethylbromoacetate ( 15 . 03 g , 0 . 09 mole ) in acetone ( 150 cm 3 ). the reaction mixture was stirred at room temperature under a nitrogen atmosphere for seventy - two hours . the solvent was evaporated under vacuum and the residue treated with ca 2n hcl ( aq ) ( 100 cm 3 ). the resultant brown solid was slurried in methanol to yield a brown coloured solid ( 8 . 26 g , 43 %). ( iii ) the tetra - alkylated pyrogallol calixarene ( 6 g , 0 . 005 mole ) in absolute ethanol ( 50 cm 3 ) was treated with koh ( 6 . 6 g , 0 . 12 mole ). the reaction mixture was stirred under reflux for two hours and filtered hot . the brown solid was washed with hot ethanol and dried in the oven to yield the product ( 7 . 26 g , 100 %). pyrogallol calixarene was prepared as outlined in example 1 ( i ). pyrogallol calixarene was then alkylated in accordance with the procedure outlined in example 1 ( ii ) except six equivalents of ethylbromoacetate and potassium carbonate were used . alkylation was carried out under reflux for three days . a mixture of compounds was obtained ( bc010302b ). pyrogallol calixarene was prepared as outlined above in example 1 ( i ). pyrogallol calixarene ( 9 . 30 g , 0 . 01 mole ) in acetone ( 100 cm 3 ) was treated with potassium carbonate ( 11 . 05 g , 0 . 08 mole ) and chloroacetic acid ( 7 . 5 g , 0 . 08 mole ) in acetone ( 50 cm 3 ) added drop wise . the reaction mixture was stirred at room temperature under a nitrogen atmosphere over night . the solution was filtered , washed with acetone , slurried in methanol and acidified with conc . hcl . the solid was then slurried in ethanol and treated with koh under reflux for 30 minutes to convert to the potassium salt . the solid was filtered and dried in a vacuum oven to yield 6 . 4 g of material . ( i ) to resorcinol ( 5 ) ( 10 g , 0 . 091 mole ) in absolute ethanol ( 40 cm 3 ) was added p - fluorobenzaldehyde ( 11 . 3 g , 0 . 091 mole ) and 37 % hcl ( aq .) ( 13 . 5 cm 3 ). the reaction mixture was stirred under reflux for five hours . after cooling , the solid precipitate was collected by filtration and washed with ethanol : water ( 4 : 1 ). the crude brown solid was then slurried under reflux in methanol , cooled , filtered and washed with cold methanol to yield 11 . 3 g ( 53 %) of a grey / white solid . resorcarene ( 4 g , 0 . 0046 mole ) was treated with potassium carbonate ( 6 . 4 g , 0 . 046 mole ) and ethylbromoacetate ( 7 . 72 g , 0 . 046 mole ) in acetone ( 50 cm 3 ). the reaction mixture was stirred at room temperature under a nitrogen atmosphere for seventy - two hours . the solvent was evaporated under vacuum and the residue treated with ca 2n hcl ( aq ) ( 30 cm 3 ). the resultant brown solid was slurried in methanol to yield an off white coloured solid ( 63 g , 87 % o ). the alkylated resorcarene ( 6 g , 0 . 004 mole ) in absolute ethanol ( 40 cm 3 ) was treated with koh ( 5 . 61 , 0 . 1 mole ). the reaction mixture was stirred under reflux for two hours and filtered hot . the white solid was washed with hot ethanol and dried in the oven to yield the product ( 6 . 31 g , ca . 100 %). it will be appreciated by those skilled in the art that the above tetra - benzyl product could be prepared by a process analogous to example 2 above . the above compound may be prepared by fully alkylating the tetra - benzyl product of example 5 and then deprotecting by removing the benzyl groups and alkylating to form the above octa - alkyl product . it will be appreciated by those skilled in the art that pre - alkylated pyrogallol such as shown below may be reacted with p - fluorobenzaldehyde to yield a definitive calixarene structure . to prove the structure of the tetra - alkyl product shown above pre - alkylated pyrogallol intermediates for cyclisation are prepared . the intermediate ( 6 ) on cyclisation with 4 - fluorobenzaldehyde can produce the tetra - alkyl ester , which on hydrolysis yields the tetra - alkyl product shown above . other possible products are analogous tetra - alkyl products ( 7 ). preparation of these products requires the preparation of alternative tetramers using alternatives to 5 - fluorobenzaldehyde . based on the precedent already established , selective tetra - alkyation takes place . alternatively , the alkylating agent can be varied to produce analogous products , to probe the activity requirement of the alkyl groups . the concentration at which an hiv - 1 drug is effective is designated ec 50 μm which represents when the number of cells protected from hiv injection is half the total . the antigen agp120 assay — the virus related antigen — is related to the number of virus particles produced by measuring glycoprotein gp 120 in infected cell cultures . the concentration of the drug which reduces cell growth by 50 % is designated tc 50 μm . of course the lower the ec 50 concentration the better but the real criterion of effectiveness in in vitro testing on cell cultures is the therapeutic index which is the tc 50 / ec 50 ratio . a microtiter antigen capture elisa was developed using lectin ( gna ) from galanthus nivalis ( vector laboratories , peterborough , uk .) and human antibodies ( 10 ). the plates were coated with lectin ( 0 . 5 ug ), and after blocking with 10 % calf serum , dilutions of virus supernatant in 0 . 25 % detergent solution ( empigen , albright and wilson ltd ., whitehaven , uk .) were added to the wells and incubated at 4 ° c . for 12 - 16 hours . bound antigen was captured using human anti - hiv antibodies , and finally detected with anti - human ig antibodies conjugated to horseradish peroxidase . a selection of compounds prepared in accordance with the preceding examples were tested and compared with an original sample of ac - 1 ( 1151c ). two tests were performed : test 1 was performed using infected blood , while test 2 used cell cultures . the results are shown in table 1 which illustrates the activity of the compounds tested . the results from both tests were comparable . the activity of bc010302b was comparable to that of the sample of ac - 1 ( 1151c ). the tetra - alkylated compound bc130202a was also active , demonstrating an ec 50 of 5 μm . of the two pure compounds , the ac - 1 analogue bc130202a was slightly less active than the compound ac - 1 , while the resorcarene was much less active than the compound ac - 1 ( 1115c ). ec 50 represents the concentration which reduces the viral envelope protein gp120 interaction with the cellular receptor protein cd4 by 50 % using recombinant proteins in an immunoassay format . it has been shown that 1151c ( ac - 1 ) type compounds inhibit infection at an early stage of virus infection . this was confirmed by using recombinant proteins for the viral envelope and the cellular receptor . the proteins bind well in vitro using cd4 bound to plastic wells of 96 well plates . the results in the above table were obtained by carrying out the following procedure . all stocks solutions were made 25 mm in distilled water and tested at same concentrations . 1 plastic plates were coated with cellular receptor protein cd4 . 2 the plates were washed well before adding a predetermined , appropriate quantity of viral envelope protein gp120 for binding to cd4 . 3 to see inhibition by compounds , different concentrations were added a few minutes before adding gp120 . 4 the mixture was incubated at 37 ° c . for binding . 5 the plates were then flashed well and bound gp120 was detected by reaction with anti - hiv antibodies , incubated for 12 hours at 4 ° c . 6 the amount of antibody bound was detected by adding anti - human antibodies attached to an enzyme horse raddish peroxidase . 7 after another incubation and wash , the quantity of the enzyme was measured by adding substrate o - phenyl diamine ( opd ). 8 the colour developed was read at 492 nm . 9 all incubations took three days for adding different reagents . the percentage of inhibition by compounds , was calculated from the standard curve obtained by using different dilutions of gp120 alone . the results shown in table 1 for test 2 were obtained by testing cell cultures in accordance with the following procedure . cem cells were suspended at approximately 250 , 000 cells per milliliter of culture medium and infected with wild - type hiv - 1 ( 111 a ) at approximately 100 times the 50 % cell culture infective dose ( ccid 50 ) per milliliter . then 100 μl of the infected cell suspensions were added to 200 μl microtiter plate wells containing 100 μl of an appropriate dilution of the test compounds . after 4 days incubation at 37 ° c . the cell cultures were microscopically examined for syncytium formation . the ec 50 ( 50 % effective concentration ) was determined as the compound concentration required to inhibit syncytium formation by 50 %. the results above demonstrate that a partially alkylated product compound as defined herein , in particular a tetra - alkyl product of formula i or a product of formula i containing 6 to 8 alkyl groups is required in order for the compound to be active . it will be appreciated by those skilled in the art that a partially alkylated product may be prepared by conducting selective alkylation under suitable reaction conditions . the words “ comprises / comprising ” and the words “ having / including ” when used herein with reference to the present invention are used to specify the presence of stated features , integers , steps or components but does not preclude the presence or addition of one or more other features , integers , steps , components or groups thereof . 1 . aids and the immune system by w . c . greene scientific american 1993 p 67 . 2 . drug cocktails fight hiv by l . gopinath , chemistry in britain june 1997 p 38 and personal communications from dr . sam mcconkey , senior lecturer , department of medicine , oxford university , united kingdom and dr . peter mugyenyi , director joint clinical research centre , kampala uganda . 3 . azt benefit in doubt , chemistry in britain , may 1993 , p 62 . 4 . defeating aids : what will it take ?, scientific american , july 1998 , p 62 . 5 . potential mechanism for sustained antiretro - viral efficacy of azt - 3tc combination therapy by b . a . larder , s . d . kemp and p . r . harrigan . science vol . 269 , 4 aug . 1995 , p 696 . 6 . protease inhibitors in patients with hiv disease by m . barry , s . gibbons , d . back and f . mulcahy in clinical pharmacokinetics , march 32 ( 3 ) 1997 p 194 . 7 . pharmacokinetics and potential interactions amongst antiretroviral agents used to treat patients with hiv infection by m . barry , f . mulcahy , c . merry , s . gibbons and d . back , clinical pharmacokinetics , april 36 ( 4 ) 1999 p 289 . 8 . molecular targets for aids therapy by h . mitsuya , r . yarchoan and s . broder , science 28 sep . 1990 p 1533 . 9 . n . mahmood , a . j . hay ( 1992 ) an elisa utilizing immunobilised snowdrop lectin gna for the detection of envelope glycoproteins of hiv and siv . j . immunol methods 151 : 9 - 13 . 10 . r . pauwels , j . balazarini , m . baba , r . snoeck , d . schols , p . herdewijn , j . desmyter and e . de clerq , ( 1988 ) rapid and automated tetrazolium based colorimetric assay for the detection of anti - hiv compounds . j . virol methods 20 : 309 - 321 .