chemistry

Tirilazad

Tirilazad is a chemistry topic covered in the lgStudy science library. This page brings together a partial reference excerpt, illustrations, worked examples, real-world applications and a short study plan, so you can understand Tirilazad rather than just read about it. In short: Tirilazad is a drug that has been proposed to treat acute ischaemic stroke. When tested on animal models, tirilazad protects brain tissue, and reduces brain damage.

Key takeaways

Tirilazad belongs to chemistry; place it in that map before memorising details.
Learn the definition first, then one example that makes the definition concrete.
Connect Tirilazad to a quantity you can measure, compute or draw — that is where exam questions come from.
Reproduce the core statement of Tirilazad from memory before moving on to harder problems.

Reference excerpt

Tirilazad is a drug that has been proposed to treat acute ischaemic stroke. When tested on animal models, tirilazad protects brain tissue, and reduces brain damage. However, the drug failed to demonstrate efficacy in humans and may even worsen stroke-related outcomes. Tirilazad is a 21-aminosteroid and belongs to the "Lazaroid" family of agents. The metabolite of tirilazad is called U-89678 [157744-31-5]. Other known lazaroids found in the data base include the following list of agents: U-74389G [153190-29-5], U-74500 [111640-85-8], U-75412E [130590-09-9] & U-87999 [177949-23-4]. The name comes from Lazarus — the biblical figure raised from the dead — because these compounds were thought to “bring cells back to life” after oxidative injury. More recently Tirilazad has shown some promising results in treating traumatic brain injury (TBI).

Synthesis The chemical synthesis has been reported:Patent (Example 83; S22 page 59, A22 page 47): Precursor patent:

The starting material is called 21-Hydroxypregna-1,4,9(11),16-tetraene-3,20-dione 21-acetate [37413-91-5] (1). Soft addition of methylmagnesium chloride in the presence copper propionate (c.f. Gilman reagent), followed by saponification of the ester group furnished 21-Hydroxy-16alpha-methylpregna-1,4,9(11)-triene-3,20-dione [56016-90-1] (2). FGI of the hydroxy group to the tosyl leaving group, followed by displacement with sodium iodide led to 21-Iodo-16alphamethylpregna-1,4,9(11)-triene-3,20-dione, PC14878745 (3). The reaction of 2,4,6-Trichloropyrimidine [3764-01-0] (4) with 2 equivalents of Pyrrolidine [123-75-1] (5) gave 4-chloro-2,6-di(pyrrolidin-1-yl)pyrimidine [111669-15-9] (6). Further reaction of the remaining halogen with piperidine [110-89-4] (7) yielded 4-(Piperazin-1-yl)-2,6-di(pyrrolidin-1-yl)pyrimidine [111641-17-9] (8). Convergent synthesis between 3 and 8 completed the synthesis of tirilazad (9). N.B The precursor 4-chloro-2,6-di(pyrrolidin-1-yl)pyrimidine [111669-15-9] (6) finds dual use in the synthesis of 2-MAC (U-78517F) [122003-11-6] as well as for U-83836E (aka PNU-83836E or GNF-Pf-3881) [137018-55-4]. These agents show similar antiinflammatory/antioxidant activity to lazaroids but are not related to steroid hormones.

References

Illustrations

Worked examples

Example 1 — a first encounter with Tirilazad

Start with the simplest possible case. Write down what Tirilazad claims or describes in one sentence, then invent the smallest concrete situation in which that sentence is true. In chemistry, the smallest case is usually a single object, a single equation or a single measurement. Check that every symbol or term in your sentence has a meaning in that case.

Example 2 — changing one variable

Take the situation from Example 1 and change exactly one quantity: double it, halve it, or set it to zero. Predict what should happen to Tirilazad before you calculate. Comparing your prediction with the result is the fastest way to find out whether you understand the idea or only the words.

Example 3 — an exam-style question

Typical questions about Tirilazad ask you to (a) state it precisely, (b) apply it to given data, and (c) explain a limitation. Practise writing all three answers in under five minutes; the third part is what separates a full-mark answer from an average one.

Applications of Tirilazad

In research: Tirilazad appears in chemistry research whenever the underlying quantities have to be modelled precisely. Papers usually cite it as a starting assumption and then explore where it breaks down.
In technology and industry: Engineering practice reuses Tirilazad in design rules, simulations and safety margins. Knowing the idea lets you read a specification sheet and understand why the numbers look the way they do.
In the classroom: Tirilazad is common in secondary-school and first-year university syllabi. It links to neighbouring topics 1-(2-Pyrimidinyl)piperazines, 1-Pyrrolidinyl compounds, Aminopyrimidines, so understanding it makes those chapters shorter.
In everyday life: Look for Tirilazad outside the textbook — in sport, cooking, traffic, electronics or the sky above you. An example you found yourself is remembered far longer than one you were given.

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How to study Tirilazad in 20 minutes

Read the reference excerpt below once, without taking notes.
Close the page and write down what Tirilazad means in your own words.
Compare your version with the excerpt and mark what you missed.
Work through the three examples above with pen and paper.
Explain Tirilazad out loud to somebody else — or to Teacher Smith in the lgStudy chat.

Frequently asked questions

What is Tirilazad in simple terms?

Tirilazad is a drug that has been proposed to treat acute ischaemic stroke. When tested on animal models, tirilazad protects brain tissue, and reduces brain damage.

Why does Tirilazad matter?

Because it connects several chemistry ideas at once: it gives you a definition you can apply, a quantity you can calculate, and a way to check whether a result is plausible.

How should I study Tirilazad?

Read the excerpt, restate it from memory, then work through the examples and applications listed on this page. The five-step study plan above takes about twenty minutes.

What does this page cover?

It gives you a compact reference excerpt plus original lgStudy explanations, examples, applications and study material on Tirilazad.