In terms of sheer size and power, a Star destroyer blows most Trek ships out of the water. I don't think Lucas was limited by any kind of loyalty to realism or even reasonable thought when designing SW stuff, it was more about what looked cool.
A Borg Cube on the other hand, that would be more of a challenge. Much more comparable size and crew wise, much better shields, transporters, drones and their nano-tech.
A Cube might even be able to take on the death star
My response:
Assuming, for the moment, that the Enterprise is at least capable of SURVIVING 60 seconds of combat with a Star Destroyer, then what will most likely happen is that the Enterprise runs away and devises a technobabble workaround - modulating their shields to counter disruptor fire, beaming a torpedo on board the Star Destroyer, you get the idea - that then defeats the Star Destroyer. Because the Star Destroyer is crewed by soldiers, while the Enterprise is crewed by scientists and engineers.
Isn't the Enterprise also supposed to serve as a science and exploration vessel, instead of a warship? It can obviously put up a good fight, but it wasn't built primarily as a war machine. A typical Star Destroyer is equipped with 60 laser batteries and 10 fighter squadrons, and that's without factoring the ground forces they can carry.
As to the transporter idea, those don't work through shields IIRC; they wouldn't be able to leave any toys in an ISD without either dropping the shields or sending them in preemptively, which has never been Picard's style.
Some things I feel I required to point out and for this I want to go beyond just the
Enterprise and will, instead, talk about the Federation as a whole:
1: In Star Trek we have seen the Federation use a number of different combat tactics at both close and long range. In the TNG episode The Wounded, for example, we see a
Nebula-class starship, the U.S.S.
Phoenix, engaging a Cardassian warship at a range of around 300,000 km while in the DS9 episode Sacrifice of Angels we see a Federation fleet engaging a Dominion fleet at point blank range while also using a number of attack fighters in their opening assault. I have never seen any Star Destroyer of any type in Star Wars that engaged a target that wasn't right on top of them so this tells me that the Feds have the advantage in range when it comes to their weapons.
2: The Feds have fighters at their disposal.
3: The Feds have shown an ability to field stupidly large number of ships by the time they were at war with the Dominion. Starfleet's Seventh Fleet fielded 112 ships during an engagement with the Dominion. By the time Starfleet decided to launch Operation Return they had a fleet of ships numbering in excess of 300. I seem to recall that the Empire's fleet at the Battle of Endor boasted the largest imperial fleet assembled. I just looked it up and, not counting the Death Star (I'm not including space stations), there were a grand total of 37 ships fighting for the Emperor. Even if we discount my recollection, this was supposed to be the battle that would crush the Rebel Alliance for good, so you'd want the largest fleet you could get. That tells me that the Feds would outnumber the Empire in that battle by just over 8 to 1. Those are some pretty damn good odds if you ask me, especially considering the Feds could park outside of the Empire's weapons range and rain hell down on them.
4: The
Enterprise-D (pictured) was a
Galaxy-class starship. The
Galaxy-class were an exploration and science vessels but they were considered one of the Federation's most powerful ships and stayed at that spot with over 6 ships commissioned and even served as the backbone of the Federation's war efforts as capitol ships until the development of the
Defiant-class.
Defiant-class starships were developed when the Starfleet Corps of Engineers basically said "Why don't we just strap some big guns to a bigger engine?" The
Defiant-class was designed as nothing more than a warship to be small, very hard hitting, and as agile as a fighter with the stated goal of taking on fucking Borg CUBES. Gul Dukat called it the most powerful warship in the quadrant. And then the SCOE said "The
Defiant was a good start. Okay, that's good. But how about if we make something even more badass?" And then they came up with the
Akira-class, a ship designed to be a carrier/flying torpedo launcher. It has fifteen torpedo tubes on it so it can provide cover for fighters as they launch and are recovered. And then the SCOE said "Okay, that's good too. But how about if we make something even more badass?" And then they came up with the
Prometheus-class, a ship that can separate into three warp capable sections each one powerful enough to tackle a Romulan Warbird on their own. And then the
Sovereign-class was commissioned and the SCOE saw that it was good and on the seventh day they rested.
"I've found it wise never to under estimate the Federation's technical skill." ~ Gul Dukat